Pyrazole-glycolic acid amide derivatives as herbicides

ABSTRACT

Pyrazole-glycolic acid amides of the following formula (1) (in which R 1  to R 5  each represent a hydrogen atom or a substituent having a broad definition), and herbicides containing them. The compounds have a high herbicidal effect against paddy weeds, especially Echinochloa crus-galli, while highly safe for paddy rice plants. ##STR1##

This application is 371 of PCT/JP92/01476 filed on Nov. 12, 1995.

TECHNICAL FIELD

The present invention relates to novel pyrazole-glycolic acid amide derivatives and to herbicides containing them as the active ingredients.

BACKGROUND ART

At present, a lot of herbicides have been put to practical use as those applicable to paddy fields, and they are popularly used as single products or combination products.

Herbicides may be applied to various kinds of paddy weeds. A lot of herbicides effective against annual broad-leaved weeds are known, and herbicides effective against perennial weeds are increasing in these several years.

However, since Echinochloa crus-galli, which is one serious paddy weed and which grows mostly in large areas of paddy fields, belongs to the same family of Gramineae as a paddy rice plant belongs to, herbicides which are effective against only, Echinochloa crus-galli, especially those that have grown tall, without injuring paddy rice plants at all are not almost known.

As the prior art relating to compounds which are similar to the compounds of the present invention with respect to their chemical structures, compounds having a glycolic acid amide moiety bonded to the 2-position of a benzothiazole ring have been disclosed in JP-A 54-154762, compounds having the same moiety bonded to a 5-membered aromatic mono-cyclic ring containing an oxygen atom or a sulfur atom along with from 1 to 3 nitrogen atoms have been disclosed in JP-A 55-147267, compounds having the same moiety bonded to the 5-position of a tetrazole ring have been disclosed in JP-A 56-86175, and compounds having the same moiety bonded to the 5-position of an isoxazole ring have been disclosed in JP-A 63-152367. However, compounds having a glycolic acid amide moiety bonded to a pyrazole ring, such as those of the present invention, are not known at all up to the present and are novel compounds.

DESCRIPTION OF THE INVENTION

We, the present inventors have continued assiduous studies for many years so as to develop herbicides that are selectively effective against only harmful weeds without injuring important crop plants, while having investigated a lot of compounds with respect to their herbicidal activity so as to create herbicidal compounds which have a higher herbicidal activity and a broader selectivity in the activity. As a result, we have found that pyrazole-glycolic acid amide derivatives of the following formula (1) (hereinafter referred to as compounds of the present invention) have a high herbicidal activity against Echinochloa crus-galli and other paddy weeds, while having a high safety for paddy rice plants, and that the derivatives are effective even when a small amount of them is used. On the basis of these findings, we have completed the present invention. ##STR2## wherein

R¹ represents a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₆ cycloalkyl group, a C₂₋₄ alkenyl group, a C₂₋₄ alkynyl group, a C₃₋₆ cycloalkyl-substituted C₁₋₂ alkyl group, a C₁₋₄ haloalkyl group, a di-C₁₋₄ alkylamino-C₁₋₄ alkyl group, a C₁₋₄ alkoxy-C₁₋₄ alkyl group, a C₁₋₄ alkylthio-C₁₋₄ alkyl group, a C₁₋₄ alkylsulfinyl-C₁₋₄ alkyl group, a C₁₋₄ alkylsulfonyl-C₁₋₄ alkyl group, a phenyl-substituted C₁₋₄ alkyl group, a phenyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a C₁₋₄ alkoxy group, a C₁₋₄ haloalkoxy group, a benzyloxy group, a C₁₋₄ alkylthio group, a benzylthio group, a C₁₋₄ alkylsulfinyl group, a C₁₋₄ alkylsulfonyl group, a di-C₁₋₄ alkylsulfamoyl group, a cyano group, a halogen atom, a di-C₁₋₄ alkylamino group or a nitro group;

R² represents a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₆ cycloalkyl group, a C₂₋₄ alkenyl group, a C₂₋₄ alkynyl group, a C₃₋₆ cycloalkyl-substituted C₁₋₂ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkylcarbonyl-C₁₋₄ alkyl group, a C₁₋₄ alkoxycarbonyl-C₁₋₄ alkyl group, a di-C₁₋₄ alkylamino-C₁₋₄ alkyl group, a C₁₋₄ alkoxy-C₁₋₄ alkyl group, a C₁₋₄ alkoxy-C₁₋₄ alkoxy-C₁₋₄ alkyl group, a C₁₋₄ alkylthio-C₁₋₄ alkyl group, a C₁₋₄ alkylsulfinyl-C₁₋₄ alkyl group, a C₁₋₄ alkylsulfonyl-C₁₋₄ alkyl group, a phenyl-substituted C₁₋₄ alkyl group, a phenyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a naphthyl group, a pyridyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a C₁₋₄ alkylcarbonyl group, a C₁₋₄ alkylaminocarbonyl group, a di-C₁₋₄ alkylaminocarbonyl group, a C₁₋₄ alkoxycarbonyl group, a C₁₋₄ alkylsulfonyl group or a di-C₁₋₄ alkylsulfamoyl group;

R³ represents a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₆ cycloalkyl group, a C₂₋₄ alkenyl group, a C₂₋₄ alkynyl group, a phenyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a cyano group, a halogen atom or a nitro group;

R⁴ and R⁵ independently represent a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₆ cycloalkyl group, a C₂₋₄ alkenyl group, a C₂₋₄ alkynyl group, a C₃₋₆ cycloalkyl-substituted C₁₋₂ alkyl group, a C₁₋₄ alkoxy-C₁₋₄ alkyl group, a phenyl-substituted C₁₋₄ alkyl group (in which the phenyl moiety may be optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a phenyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a pyridyl-substituted C₁₋₄ alkyl group (in which the pyridyl moiety may be optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a pyridyl group (optionally substituted by one or more substituents selected from a C₁₋₄ alkyl group, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxy group, a cyano group, a nitro group and a halogen atom), a naphthyl group, a naphthyl-substituted C₁₋₄ alkyl group, a C₁₋₄ alkoxy group (provided that both R⁴ and R⁵ must not be alkoxy groups), a cyano-C₁₋₄ alkyl group, a C₁₋₄ alkylcarbonyl group, a C₁₋₄ alkoxycarbonyl group, a C₁₋₄ alkoxycarbonyl-C₁₋₄ alkyl group or a C₁₋₄ alkylsulfonyl group; and

R⁴ and R⁵ may form, along with the nitrogen atom to which they bond, a 3-membered to 9-membered ring; and the ring may have one or more oxygen atoms, sulfur atoms, nitrogen atoms, carbonyl groups, sulfonyl groups or unsaturated bonds, the ring may be substituted by a C₁₋₄ alkyl group, a C₁₋₄ alkoxy group, a hydroxyl group, a halogen atom, a C₁₋₄ haloalkyl group, a C₁₋₄ alkoxycarbonyl group, a phenyl group or a benzyl group, the ring may be crosslinked with a C₁₋₄ alkylene, and the ring may be condensed with a benzene ring.

Examples of the substituents R¹, R², R³, R⁴ and R⁵ in the compounds of the present invention are mentioned hereunder, while the definitions of the abbreviated expressions used therein are mentioned below.

Me: methyl group

Et: ethyl group

Pr-n: normal propyl group

Pr-iso: isopropyl group

Bu-n: normal butyl group

Bu-iso: isobutyl group

Bu-sec: secondary butyl group

Bu-tert: tertiary butyl group

Pen-n: normal pentyl group

Hex-n: normal hexyl group

Pr-cyc: cyclopropyl group

Bu-cyc: cyclobutyl group

Pen-cycl: cylopentyl group

Hex-cyc: cyclohexyl group

Ph: phenyl group

Py: pyridyl group

Naph: naphthyl group

Examples of the substituent R₁ in the compounds of the present invention:

H, Me, Bt, Pr-n, Pr-iso, Bu-n, Bu-iso, Bu-sec, Bu-tert, Pen-n, Hex-n, Hex-iso, Pr-cyc, Bu-cyc, Pen-cyc, Hex-cyc, CH₂ CH═CH₂, CH₂ CH═CHMe, CH₂ CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ C.tbd.CMe, CH₂ Pr-cyc, CH₂ Bu-cyc, CH₂ Pen-cyc, CH₂ Hex-cyc, CH₂ CH₂ Pr-cyc, CH₂ F, CH₂ Cl, CH₂ Br, CH₂ I, CHF₂, CHCl₂, CHBr₂, CF₃, CCl₃, CBr₃, CClF₂, CF₃ CH₂, CF₃ CF₂ CF₂, Cl CH₂ CH₂ CH₂, ClCH₂ CH₂ CH₂ CH₂, CH₂ NMe₂, CH₂ NEt₂, CH₂ N(Pr-n)₂, CH₂ N(Pr-iso)₂, CH₂ N(Bu-n)₂, CH₂ CH₂ CH₂ CH₂ NMe₂, CH₂ OMe, CH₂ OEt, CH₂ OPr-n, CH₂ OBu-n, CH₂ OBu-iso, CH₂ OBu-sec, CH₂ OBu-tert, CH₂ CH₂ OMe, CH₂ CH₂ OEt, CH₂ CH₂ OPr-n, CH₂ CH₂ CH₂ OMe, CH₂ CH₂ CH₂ OEt, CH₂ CH₂ CH₂ CH₂ OMe, CH₂ SMe, CH₂ SEt, CH₂ SPr-n, CH₂ SBu-n, CH₂ CH₂ CH,CH₂ SMe, CH₂ S(O)Me, CH₂ S(O)Et, CH₂ S(O)Pr-n, CH₂ S(O)Bu-n,, CH₂ CH₂ CH₂ CH₂ S(O)Me, CH₂ SO₂ Me, CH₂ SO₂ Et, CH₂ SO₂ Pr-n, CH₂ SO₂ Bu-n, CH₂ CH₂ CH₂ CH₂ SO₂ Me, CH₂ Ph, CHMePh, CMe₂ Ph, Ph, 2-Cl-Ph, 3-Cl-Ph, 4-Cl-Ph, 2,4-Cl-Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-F-4-Cl-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2,4-Me₂ -Ph, 2,6-Me₂ -Ph, 2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF₃ -Ph, 3-CF₃ -Ph 4-CF₃ -Ph, 3,5-Cl₂ -Ph, 2,6-Cl₂ -Ph, 2,3-Cl₂ -Ph, 2,4,6-Cl₃ -Ph, 2,3,5-Cl₃ -Ph, 2,3,4-Cl₃ -Ph, 2-NO₂ -Ph, 2-CN-Ph, OMe, OEt, OPr-n, OPr-iso, OBu-n, OBu-iso, OBu-tert, OCH₂ F, OCBrF₂, OCHF₂, OCF₃, OCH₂ CH₂ Cl, OCH₂ CH₂ CH₂ CHCl, OCH₂ Ph, SMe, SEt, SPr-n, SPr-iso, SBu-n, SBu-iso, SBu-tert, SCH₂ Ph, S(O)Me, S(O)Et, S(O)Pr-n, S(O)Pr-iso, S(O)Bu-n, SO₂ Me, SO₂ Et, SO₂ Pr-n, SO₂ Pr-iso, SO₂ Bu-n, SO₂ NMe₂, SO₂ NEt₂, SO₂ N(Pr-n)₂, SO₂ N(Bu-n)₂, CN, F, Cl, Br, I, NMe₂, NEt₂, N(Pr-n)₂, N(Pr-iso)₂, N(Bu-n)₂, NO₂

Examples of the substituent R² in the compounds of the present invention:

H, Me, Bt, Pr-n , Pt-iso, Bu-n, BU-iso, Bu-sec, Bu-tert, Pen-n, Hex-n, Pr-cyc, Bu-cyc, Pen-cyc, Hex-cyc, CH₂ CH|CH₂. CH₂ CH|CHMe, CH₂ CH₂ CH|CH₂, CH₂ C.tbd.CH₂ C.tbd.CMe, CH₂ Pr-cyc, CH₂ Bu-cyc, CH₂ Pen-cyc, CH₂ Hex-cyc, CH₂ CH₂ Pr-cyc, CH₂ F, CH₂ Cl, CH₂ Br, CH₂ I, CHF₂, CHCl₂, CHBr₂, CF₃, CCl₃, CBr₃. CClF₂, CF₃ CH₂, CF₃ CF₂, CF₃ CF₂ CF₂, ClCH₂ CH₂ CH₂, ClCH₂ CH₂ CH₂, CH₂, CH₂ COMe, CH₂ COBt, CH₂ COPr-n, CH₂ COPr-iso, CH₂ COBu-n, CHMeCOMe, CHMeCOBt, CHMeCOPr-n, CH₂ CH₂ CH₂ COMe, CH₂ CO₂ Me, CH₂ CO₂ Bt,CH₂ CO₂ Pr-n, CH₂ CO₂ Pr-iso, CH₂ CO₂ Bu-n, CHMeCO₂ Me, CHMeCO₂ Bt, CHMeCO₂ Pr-n, CH₂ CH₂ CH₂ CO₂, CH₂ NMe₂, CH₂ NBt₂, CH₂ N(Pr-n)₂, CH₂ N(Pr-iso)₂, CH₂ N(Bu-n)₂, CH₂ CH₂ CH₂ CH₂ NMe₂, CH₂ OMe, CH₂ OBt, CH₂ OPr-n, CH₂ OBu-n, CH₂ OBu-iso, CH₂ OBu-sec, CH₂ OBu-tert, CH₂ CH₂ OMe, CH₂ CH₂ OBt, CH₂ CH₂ OPr-n, CH₂ CH₂ CH₂ OMe, CH₂ CH₂ CH₂ OBt, CH₂ CH₂ CH₂ CH₂ OMe, CH₂ OCH₂ CH₂ OMe, CH₂ OCH₂ CH₂ OBt, CH₂ SBt, CH₂ SPr-n, CH₂ SBu-n, CH₂ CH₂ CH₂ CH₂ SMe, CH₂ S(O)Me, CH₂ S(O)Bt, CH₂ S(O)Pr-n, CH₂ S(O)Bu-n, CH₂ CH₂ CH₂ CH₂ S(O)Me, CH₂ SO₂ Me, CH₂ SO₂ Bt, CH₂ SO₂ Pr-n, CH₂ SO₂ Bu-n, CH₂ CH₂ CH₂ CH₂ SO₂ Me, CH₂ Ph, CHMePh, CMe₂ Ph, Ph, 2-Cl-Ph, 3-Cl-Ph, 4Cl-Ph, 2,4-Cl₂ Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-F-4-Cl-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2,4-Me₂ Ph, 2,6-Me₂ -Ph, 2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF₃ -Ph, 3CF₃ -Ph, 4-CF₃ -Ph, 3,5-Cl₂ -Ph, 2,6-Cl₂ -Ph, 2,3-Cl₂ -Ph, 2,4,6-Cl₃ -Ph, 2,3,5-Cl₃ Ph, 2,3,4-Cl₃ Ph, 2-Cl-4-CF₃ -Ph, 2,6-Cl₂ -4-CF₃ -Ph,

2-NO₂ -Ph, 2-CN-Ph, 3-CN-Ph, 4-CN-Ph, 1-Naph, 2-Naph, COMe, COBt, COPr-n, COPr-iso, COBu-n, CONHMe, CONHBt, CONHPr-n, CONHPr-iso, CONHBu-n, CONMe₂, CONBt₂, CON(Pr-n)₂, CON(Pr-iso)₂, CON(Bu-n)₂, CO₂ Me, CO₂ Bt, CO₂ Pr-n, CO₂ Pr-iso, CO₂ Bu-n, SO₂ Me,SO₂ Bt, SO₂ Pr-n, SO₂ Pr-iso, SO₂ Bu-n, SO₂ NMe₂, SO₂ NBt₂, SO₂ N(Pr-n)₂, SO₂ N(Bu-n)₂, 2,5-Cl₂ -Ph, 3,4-Cl₂ -Ph, 2,4-(NO₂)₂ -Ph, 3-NO₂ -Ph, 4-NO₂ -Ph, 2-Py, 3-Py, 4-Py, 3-Cl-2-Py, 4Cl-2-Py, 5Cl-2-Py, 6-Cl-2-Py, 3-F-2-Py, 4-F-2-Py, 5-F-2-Py, 6F-2-Py, 3-Br-2-Py, 4-Br-2-Py, 5-Br-2-Py, 6-Br-2-Py, 3-CF₃ -2Py, 4CF₃ -2-Py, 5-CF₃ -2-Py, 6-CF₂ -Py, 3-Cl-5-CF₃ -2Py, 3Me-2-Py, 4Me-2-Py, 5-Me-2-Py, 6-Me-2-Py, 3-NO₂ 2-Py, 4-NO₂ -2-Py, 5-NO₂ -Py, 6-NO₂ -2-Py, 3-Py, 4-Py

Examples of the substituent R³ in the compounds of the present invention:

CN, F, Cl, Br, I, NO₂, H, Me, Bt, Pr-n, Pr-iso, Bu-n, Bu-iso, Bu-sec, Bu-tert, Pen-n, Hex-n, Hex-iso, Pr-cyc, Bu-cyc, Pen-cyc, Hex-cyc, CH₂ CH|CH₂, CH₂ CH═CHMe, CH₂ CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ C.tbd.CMe, Ph, 2-Cl-Ph, 3-Cl-Ph, 4-Ph, 2,4-Cl₂ -Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2F-4-Cl-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2,4-Me₂ -Ph, 2,6-Me₂ -Ph, 2-MeO-Ph, 3MeO-Ph, 4MeO-Ph, 2-CF₈ -Ph, 3-CF₈ -Ph, 4-CF₈ -Ph, 3,5-Cl₂ -Ph, 2,6-Cl₂ -Ph, 2,3-Cl₂ -Ph, 2,4,6-Cl₈ -Ph, 2,3,5-Cl₃ 2,3,4-Cl₃ -Ph, 2-NO₂ -Ph, 2-CN-Ph

Examples of the substituents R⁴ and R⁵ in the compounds of the present invention: H, Me, Bt, Pr-n, Pr-iso, Bu-n, Bu-iso, Bu-sec, Bu-tert, CHMeCHMe₂, Pen-n, Hex-n, Hex-iso, Pr-cyc, Bu-cyc Pen-cyc, Hex-cyc, CH₂ Pr-cyc, CH₂ Bu-cyc, CH₂ Hex-cyc, CH₂ CH₂ Pr-cyc, CH₂ CH═CH₂, CH₂ CH|CHMe, CH₂ CH₂ CH═CH₂, CH₂ C.tbd.CH, CH₂ C.tbd.CMe, CH₂ Ome CH₂ OBt, CH₂ OPr-n, CH₂ OBu-n, CH₂ OBu-iso, CH₂ OBu-sec, CH₂ OBu-tert, CH₂ CH₂ Ome CH₂ CH₂ OBt, CH₂ CH₂ OPr-n, CH₂ CH₂ CH₂ OMe, CH₂ CH₂ CH₂ OBt, CH₂ CH₂ CH₂ CH₂ OMe, Ph, 2Cl-Ph, 3-Cl-Ph, 4-Cl-Ph, 2,4-Cl₂ -Ph, 3,5-Cl₂ -Ph, 2,6-Cl₂ -Ph, 2,3-Cl₂ -Ph, 2,5-Cl₂ -Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-F-4-Cl-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2,4-Me₂ Ph, 3,5-Me₂ -Ph, 2,6-Me₂ -Ph, 2,3-Me₂ Ph, 2,5Me₂ -Ph, 2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF₈ -Ph, 3-CF₈ -Ph, 4-CF₈ -Ph, 2,4,6-CL₈ -Ph, 2,3,5-Cl₈ -Ph, 2,3,4-Cl₈ Ph, 2-NO₂ -Ph, 2-CN-Ph, CH₂ -Ph, OMe, OBt, OPr-n, OPr-iso, OBu-n, OBu-iso, OBu-tert, SO₂ Bt, SO₂ Pr-n, SO₂ Pr-iso, SO₂ Bu-n, COMe, COBt, COPr-iso, COBu-n, CO₂ Me, CO₂ Bt, CO₂ Pr-n, CO₂ Pr-iso, CO₂ Bu-n, CH₂ CO₂ Me, CH₂ CO₂ Bt, CH₂ CO₂ Pr-n, CH₂ CO₂ Bu-n, CHMeCO₂ Me, CHMeCO₂ Bt, CH₂ CH₂ CO₂ Me, CH₂ CH₂ CH₂ CO₂ Me, CH₂ CH₂ CH₂ CH₂ CO₂ Me, CH(Pr-iso)CO₂ Me, CH(Bu-sec)CO₂ Me, CH(Bu-iso)CO₂ Me, CH(CH₂ Ph)CO₂ Me, CH₂ CH₂ CN, 1 Naph, 2-Naph, CH₂ -1-Naph, CH₂ -2-Naph, CH₂ Ph, CHMePh, CMe₂ Ph, CH₂ -Cl-Ph, CH₂ -3-Cl-Ph, CH₂ -4-Cl-Ph, 2-Py, 6-MeO-2-Py, 6-Cl-2-Py, 6F-2-2-Py, 5-CF₈ -2-Py, 3-Cl-5-CF₈ -2-Py, 3-Py, 4-Py, CH₂ -5-Cl-2-Py, CH₂ -6-Cl-3-Py

Examples of saturated 5-membered to 7-membered rings to be formed by the substituents R⁴ and R⁵ along with the nitrogen atom to which they bond in the compounds of the present invention: ##STR3##

The compounds of the present invention may be produced easily in accordance with anyone of the following reaction schemes 1 to 4.

Reaction Scheme 1: ##STR4## wherein R¹, R², R³, R⁴ and R⁵ have the same definitions as those mentioned above, and Z represents a halogen atom.

Precisely, a 5-halogenopyrazole (2) is reacted with a glycolic acid amide (3) in the presence of a base to produce the compound (1) of the present invention. As the base, usable are inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium hydride, etc.; or organic bases such as pyridine, triethylamine, DBU, etc. This reaction may progress even in the absence of a solvent but, if desired, may be conducted in the presence of a solvent. The solvent usable in the reaction is not specifically defined, provided that it is inert to the reaction. As the usable solvents, for example, mentioned are aliphatic or aromatic hydrocarbons such as hexane, cyclohexane, benzene, toluene, etc.; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; nitriles such as acetonitrile, propionitrile, etc.; acid amides such as dimethylformamide, dimethylacetamide, etc.; sulfones such as dimethylsulfoxide, sulforane, etc.; and organic bases such as pyridine, etc. The reaction temperature may be freely selected from the range between -50° C. and 150° C. but is preferably within the range between 0° C. and 60° C.

Reaction Scheme 2: ##STR5## wherein R¹, R², R³, R⁴, R⁵ and Z have the same definitions as those mentioned above.

Precisely, a 5-hydroxypyrazole (4) is reacted with a halogenoacetamide (5) in the presence of a base to produce the compound (1) of the present invention. As the base and the solvent, those mentioned for the reaction scheme 1 shall be referred to. The reaction temperature may be freely selected from the range between -50° C. and 150° C. but is preferably within the range between 0° C. and 100° C.

Reaction Scheme 3: ##STR6## wherein R¹, R², R³, R⁴ and R⁵ have the same definitions as those mentioned above, and X represents a nitro group or a halogen atom.

Precisely, a 5-hydroxypyrazole (6) is reacted with a halogenoacetamide (5) in the presence of a base to give a pyrazole-glycolic acid amide (7). As the base, the solvent and the reaction temperature, those mentioned for the reaction scheme 1 shall be referred to. The amide (7) is then treated with a nitrating agent such as a mixed acid or the like or with an electrophilic halogenating agent such as chlorine, bromine, sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, etc., to produce the compound (1') of the present invention.

Reaction Scheme 4: ##STR7## wherein R¹, R², R³, R⁴, R⁵ and Z have the same definitions as those mentioned above, and Y represents a C₁₋₆ alkyl group or a phenyl group.

Precisely, a 5-hydroxypyrazole (4) is reacted with a halogenoacetate (8) in the presence of a base to give a pyrazole-glycolate (9). As the base, the solvent and the reaction temperature, those mentioned for the reaction scheme 1 shall be referred to. The ester (9) is then hydrolyzed and halogenated to give an acid chloride (11), which is reacted with an amine (12) to produce the compound (1) of the present invention.

Regarding the staring materials to be used in the above-mentioned reactions, 5-chloro-4-nitropyrazoles (2, Z=Cl) may be produced with reference to U.S. Pat. No. 3,282,954 (1966), etc.; 5-bromo-4-nitropyrazoles (2, Z=Br) may b produced with reference to Journal of Organic Chemistry Vol. 51, page 4656 (1986), etc.; and 5-hydroxy-4-nitropyrazoles (4) may be produced with reference to Chemiche Berichte, Vol. 74, page 1420 (1941), etc.

Examples of producing the compounds of the present invention are mentioned hereunder, which, however, are not intended to restrict the scope of the present invention.

Example 1:

(1) Production of 3,5-dichloro-1-methylpyrazole: ##STR8##

113 g (0.58 mol) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid were heated at 300° C. and distilled to give 51 g of a crude oil, which were dissolved in 200 ml of chloroform and washed with water. After removal of the solvent, 44 g of the intended product were obtained by distillation. This had a boiling point of 172° to 173° C.

(2) Production of 3,5-dichloro-1-methyl-4-nitropyrazole: ##STR9##

A solution of 8.5 g (56 mmol) of 3,5-dichloro-1-methylpyrazole in acetic anhydride (15 ml) was added dropwise to a mixed acid comprising 20 ml of concentrated sulfuric acid and 6 g of fuming nitric acid, at 20° C. or lower. After stirred for 48 hours at room temperature, this was poured into 300 ml of water with ice, whereupon the crystals thus precipitated were taken out by filtration, washed with water and dried to obtain 5.68 g of the intended product. This .had a melting point of 84° to 88° C.

(3) Production of N-methyl-N-phenyl-2-(3-chloro-1-methyl-4-nitropyrazol-5-yloxy)acetamide: ##STR10##

0.63 g (3.2 mmol) of 3,5-dichloro-1-methyl-4-nitropyrazole and 0.53 g (3.2 mmol) of N-methyl-N-phenylglycolic acid amide were dissolved in 5 ml of DMF, and 0.18 g (3.2 mmol) of powdery potassium hydroxide were added thereto. After this was stirred for 0.5 hours at room temperature, 20 ml of water were added thereto. This was extracted two times each with 20 ml of benzene, the resulting extract was washed with water and dried with anhydrous sodium sulfate. Then, the solvent was removed by distillation. A small amount of diisopropyl ether was added to the resulting residue, and the crystals thus precipitated were taken out by filtration and dried to obtain 0.7 g of the intended product. This had a melting point of 104° to 105° C.

Example 2:

(1) Production of 3-trifluoromethyl-1-methyl-5-hydroxy-4-nitropyrazole: ##STR11##

10 g (60 mmol) of 3-trifluoromethyl-1-methyl-5-hydroxypyrazole were dissolved in 30 ml of concentrated sulfuric acid, and 7 ml of 60% nitric acid were dropwise added thereto at 10° C. or lower. After stirred for 2 hours at room temperature, this was poured into 300 ml of water with ice, whereupon the crystals thus precipitated were taken out by filtration, washed with water and dried. The thus-obtained crystals were washed with a mixture of diisopropyl ether and diethyl ether and dried to obtain 5.5 g of the intended pure product. This had a melting point of 93° to 94° C.

(2) Production of N-methyl-N-phenyl-2-(3-trifluoromethyl-1-methyl-4-nitropyrazol-5-yloxy)acetamide: ##STR12##

1.0 g (4.7 mmol) of 3-trifluoromethyl-1-methyl-5-hydroxy-4-nitropyrazole and 0.95 g (5.2 mmol) of N-methyl-N-phenylchloroacetamide were dissolved in 10 ml of DMF, and 0.29 g (5.2 mmol) of powdery potassium hydroxide were added thereto and stirred for 5 hours at 80° C. After this was cooled, 30 ml of water were added thereto. Then, this was extracted two times each with 30 ml of benzene. The resulting extract was washed with water and de-watered with anhydrous sodium sulfate. The solvent was removed by distillation, and an oily residue was obtained. The residue was pulified by preparative high performance liquid chromatography to obtain 0.04 g of the intended product. This was oily.

Example 3:

Production of 2-[4-chloro-1-(2,5-dichlorophenyl)-3-trifluoromethylpyrazol-5-yloxy)acetopiperidide: ##STR13##

0.8 g (2.4 mmol) of 4-chloro-1-(2,5-dichlorophenyl)-3-trifluoromethyl-5-hydroxypyrazole and 0.56 g (2.2 mmol) of chloroacetopiperidide were dissolved in 4 ml of DMF, and 0.5 g (3.6 mmol) of potassium carbonate were added thereto and stirred for 4 hours at 80° C. After cooled, 50 ml of water were added thereto. Then, this was extracted two times each with 50 ml of diethyl ether. The resulting extract was washed with water and a saturated saline solution in order and then de-watered with anhydrous magnesium sulfate. The solvent was then removed by distillation. The residue was purified by silica gel column chromatography (using chloroform as the eluent) to obtain 0.42 g of the intended product. This had a melting point of 61° to 62° C.

Example 4:

(1) Production of 2-(3-trifluoromethylpyrazol-5-yloxy)acetopiperidide: ##STR14##

6.0 g (40 mmol) of 3-trifluoromethyl-5-hydroxypyrazole and 6.4 g (39 mmol) of chloroaceto-piperidide were dissolved in 40 ml of DMF, and 8.2 g (59 mmol) of potassium carbonate were added thereto and stirred for 4 hours at room temperature. After stirred for further 2 hours at 50° C., this was cooled. 200 ml of water were added thereto, and this was extracted two times each with 200 ml of ethyl acetate. The resulting extract was washed with a saturated saline solution and de-watered with anhydrous magnesium sulfate. Then, the solvent was removed by distillation. Diethyl ether was added to the residue, whereupon the crystals thus precipitated were taken out by filtration and dried to obtain 3.6 g of the intended product. This had a melting point of 154° to 156° C.

(2) Production of 2-(3-trifluoromethyl-1-propargylpyrazol-5-yloxy)acetopiperidide: ##STR15##

0.8 g (2.9 mmol) of 2-(3-trifluoromethylpyrazol-5-yloxy)acetopiperidide and 0.34 g (2.9 mmol) of propargyl bromide were dissolved in 4 ml of DMF, and 0.6 g (4.3 mmol) of potassium carbonate were added thereto and stirred for 18 hours at room temperature. 50 ml of water were added thereto, and this was extracted two times each with 50 ml of diethyl ether.

The resulting extract was washed with water and a saturated saline solution in order and de-watered with anhydrous magnesium sulfate. Then, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (using chloroform as the eluent) to obtain 0.75 g of a mixture comprising the intended product and its isomer of 2-(5-trifluoromethyl-1-propargylpyrazol-3-yloxy) acetopiperidide.

In the next step, the mixture was used directly as it was.

(3) Production of 2-(4-chloro-3-trifluoromethyl-1-propargylpyrazol-5-yloxy)acetopiperidide: ##STR16##

0.75 g (2.4 mmol) of the mixture of isomers, that had been obtained in (2), were dissolved in 4 ml of chloroform, and 0.19 g (1.4 mmol) of sulfuryl chloride were added dropwise thereto at 0° C. After this was stirred for 2 hours at 0° C., 20 ml of water with ice were added thereto. This was then extracted two times each with 20 ml of chloroform. The resulting extract was washed with an aqueous 10% sodium hydrogencarbonate solution and a saturated saline solution in order and de-watered with anhydrous magnesium sulfate. Then, the solvent was removed by distillation. The residue was purified by thin layer silica gel chromatography (using ethyl acetate/n-hexane=1/1 as the developer) to obtain 0.35 g of the intended product. This had a melting point of 78° to 79° C. The 2-(5-trifluoromethyl-1-propargylpyrazol-3-yloxy)acetopiperidide contained in the starting material was unreacted and recovered as an oily substance of 0.35 g.

Example 5:

(1) Production of ethyl 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetate: ##STR17##

28 g (107 mmol) of 4-chloro-3-trifluoromethyl-5-hydroxy-1-phenylpyrazole and 19.5 g (117 mmol) of ethyl bromoacetate were dissolved in 150 ml of acetonitrile, and 28 g (203 mmol) of potassium carbonate were added thereto and refluxed for one hour.

After cooled, the solid was filtrated out and the solvent was removed by distillation. 150 ml of chloroform were added to the residue, which was washed with water and de-watered with anhydrous sodium sulfate. Then, the solvent was removed by distillation, and 37 g of the intended product were obtained. This was oily.

(2) Production of 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetic acid: ##STR18##

37 g (106 mmol) of ethyl 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetate were dissolved in 100 ml of ethanol, and 40 ml of an aqueous solution of 8.5 g (213 mmol) of sodium hydroxide were added thereto. After this was stirred for one hour at room temperature, the solvent was removed by distillation and the residue was dissolved in 300 ml of water. The resulting aqueous solution was washed with 100 ml of benzene and then made acidic (pH 1) with concentrated hydrochloric acid. This was extracted three times each with 100 ml of chloroform, and the resulting extract was washed with water and de-watered with anhydrous sodium sulfate. Then, the solvent was removed by distillation and 33 g of the intended product were obtained. This had a melting point: of 93° to 96° C.

(3 ) Production of 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetyl chloride: ##STR19##

80 ml of thionyl chloride were added to 23 g (72 mmol) of 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetic acid and heated under reflux for 1.5 hours. The thionyl chloride was removed by distillation under reduced pressure, and 24 g of the intended product were obtained. This was oily.

(4) Production of N,N-diallyl-2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy) acetamide: ##STR20##

0.8 g (8.2 mmol) of diallylamine were dissolved in 10 ml of THF and 1.3 g (3.8 mmol) of 2-(4-chloro-3-trifluoromethyl-1-phenylpyrazol-5-yloxy)acetyl chloride were added thereto and stirred for one hour at room temperature. The reaction mixture was extracted by adding 50 ml of water, 100 ml of chloroform and several drops of concentrated hydrochloric acid thereto. The chloroform layer was washed with water and de-watered with anhydrous sodium sulfate. Then, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (using chloroform as the eluent) to obtain 1.3 g of the intended product. This was oily.

By the same methods as those of the above-mentioned examples, the compounds mentioned in Table 1 below were produced, where the structural formulae and the physical data of the compounds produced are shown along with those of the compounds produced in the above-mentioned examples. The definitions of the symbols used in Table 1 are mentioned below. ##STR21##

                  TABLE 1                                                          ______________________________________                                                                                Physical                                                                       Properties                                                                     (melting                                No.  R.sup.1  R.sup.2     R.sup.3                                                                             N R.sup.4 R.sup.5                                                                      point, °C.)                      ______________________________________                                         1    Cl       Me          NO.sub.2                                                                            Q.sub.1 104˜105                           2    CF.sub.3 Me          NO.sub.2                                                                            Q.sub.1 Oily                                    3    Cl       Me          NO.sub.2                                                                            Q.sub.3 129˜130                           4    Cl       Me          NO.sub.2                                                                            Q.sub.6 152˜153                           5    Cl       Me          NO.sub.2                                                                            Q.sub.31                                                                               Oily                                    6    Me       Me          NO.sub.2                                                                            Q.sub.1 108˜110                           7    Me       Me          NO.sub.2                                                                            Q.sub.3 137˜139                           8    Me       Me          NO.sub.2                                                                            Q.sub.6 126˜127                           9    Me       Me          NO.sub.2                                                                            Q.sub.31                                                                               97˜98                             10   H        Me          NO.sub.2                                                                            Q.sub.1 92˜93                             11   NO.sub.2 Me          NO.sub.2                                                                            Q.sub.1 86˜89                             12   NO.sub.2 Me          NO.sub.2                                                                            Q.sub.8 134˜135                           13   NO.sub.2 Me          NO.sub.2                                                                            Q.sub.6 128˜130                           14   NO.sub.2 Me          NO.sub.2                                                                            Q.sub.31                                                                               Oily                                    15   Br       Me          NO.sub.2                                                                            Q.sub.1 117˜122                           16   CF.sub.3 Me          Cl   Q.sub.1 65˜66                             17   Cl       Me          CN   Q.sub.1 Oily                                    18   Cl       Me          NO.sub.2                                                                            Q.sub.8 149˜151                           19   Cl       Me          NO.sub.2                                                                            Q.sub.15                                                                               163˜165                           20   Cl       Me          NO.sub.2                                                                            Q.sub.17                                                                               Oily                                    21   Cl       Me          NO.sub.2                                                                            Q.sub.42                                                                               Oily                                    22   Cl       Me          NO.sub.2                                                                            Q.sub.7 131˜132                           23   Cl       Me          NO.sub.2                                                                            Q.sub.12                                                                               206˜207                           24   Cl       Me          NO.sub.2                                                                            Q.sub.14                                                                               124˜125                           25   Cl       Me          NO.sub.2                                                                            Q.sub.9 104˜105                           26   Cl       Me          NO.sub.2                                                                            Q.sub.10                                                                               105˜106                           27   Cl       Me          NO.sub.2                                                                            Q.sub.11                                                                               112˜113                           28   Cl       Me          NO.sub.2                                                                            Q.sub.4  99˜101                           29   Cl       Me          NO.sub.2                                                                            Q.sub.5 107˜108                           30   Cl       Me          NO.sub.2                                                                            Q.sub.13                                                                               177˜178                           31   Cl       Me          NO.sub.2                                                                            Q.sub.27                                                                               Oily                                    32   Cl       Me          NO.sub.2                                                                            Q.sub.24                                                                               Oily                                    33   CF.sub.3 Me          Cl   Q.sub.9 88˜89                             34   CF.sub.3 Me          Cl   Q.sub.10                                                                               62˜63                             35   CF.sub.3 Me          Cl   Q.sub.11                                                                               91˜92                             36   CF.sub.3 Me          Cl   Q.sub.12                                                                               148˜149                           37   CF.sub.3 Me          Cl   Q.sub.14                                                                               105˜106                           38   CF.sub.3 Me          Cl   Q.sub.6 105˜107                           39   CF.sub.3 Me          NO.sub.2                                                                            Q.sub.6 136˜137                           40   CF.sub.3 Me          Br   Q.sub.1 Oily                                    41   CF.sub.3 Me          Br   Q.sub.24                                                                               Oily                                    42   CF.sub.3 Me          Br   Q.sub.6 104˜106                           43   Br       Me          NO.sub.2                                                                            Q.sub.6 82˜86                             44   Br       Et          NO.sub.2                                                                            Q.sub.6 Oily                                    45   Br       Pr-iso      NO.sub.2                                                                            Q.sub.6 Oily                                    46   Me       Me          Cl   Q.sub.1 59˜60                             47   Et       Me          Cl   Q.sub.1 65˜66                             48   Pr-n     Me          Cl   Q.sub.1 Oily                                    49   Pr-cyc   Me          Cl   Q.sub.1 Oily                                    50   CF.sub.2 Cl                                                                             Me          Cl   Q.sub.1 75˜76                             51   H        Me          Cl   Q.sub.1 Oily                                    52   H        Et          Cl   Q.sub.1 68˜70                             53   Cl       Me          CN   Q.sub.6 114˜115                           54   Pr-n     Me          NO.sub.2                                                                            Q.sub.1 91˜95                             55   Pr-n     Me          NO.sub.2                                                                            Q.sub.6 75˜78                             56   Pr-n     Me          NO.sub.2                                                                            Q.sub.3 66˜70                             57   Ph       Me          Cl   Q.sub.1 Oily                                    58   CF.sub.3 Me          NO.sub.2                                                                            Q.sub.10                                                                               100˜101                           59   CF.sub.3 Me          NO.sub.2                                                                            Q.sub.24                                                                               Oily                                    60   CF.sub.3 Me          NO.sub.2                                                                            Q.sub.31                                                                               Oily                                    61   CF.sub.3 CF.sub.2                                                                       Me          Cl   Q.sub.6 78˜80                             62   CF.sub.3 Ph          Cl   Q.sub.6 Oily                                    63   CF.sub.3 Ph          Cl   Q.sub.31                                                                               67˜68                             64   CF.sub.3 Ph          Cl   Q.sub.10                                                                               85˜86                             65   CF.sub.3 Ph          Cl   Q.sub.24                                                                               106˜108                           66   CF.sub.3 Ph          Cl   Q.sub.23                                                                               Oily                                    67   CF.sub.3 2-Py        Cl   Q.sub.31                                                                               108˜109                           68   CF.sub.3 CF.sub.2                                                                       Me          Cl   Q.sub.27                                                                               Oily                                    69   CF.sub.3 Me          Cl   Q.sub.27                                                                               Oily                                    70   CF.sub.3 Me          Cl   Q.sub.13                                                                               131˜132                           71   3-ClPh   Me          Cl   Q.sub.6 Oily                                    72   CF.sub.3 Ph          Cl   Q.sub.32                                                                               74˜75                             73   CF.sub.3 Ph          Cl   Q.sub.2 129˜130                           74   CF.sub.3 2-MePh      Cl   Q.sub.31                                                                               82˜83                             75   CF.sub.3 3-MePh      Cl   Q.sub.31                                                                               Oily                                    76   CF.sub.3 4-MePh      Cl   Q.sub.31                                                                               86˜87                             77   CF.sub.3 Ph          Cl   Q.sub.1 79˜80                             78   CF.sub.3 2-ClPh      Cl   Q.sub.31                                                                               53˜54                             79   CF.sub.3 3-ClPh      Cl   Q.sub.31                                                                               64˜65                             80   CF.sub.3 4-ClPh      Cl   Q.sub.31                                                                               Oily                                    81   CF.sub.3 Ph          Cl   Q.sub.19                                                                               Oily                                    82   CF.sub.3 2-ClPh      Cl   Q.sub.23                                                                               Oily                                    83   CF.sub.3 3-ClPh      Cl   Q.sub.23                                                                               Oily                                    84   CF.sub.3 4-ClPh      Cl   Q.sub.23                                                                               Oily                                    85   CF.sub.3 2-BrPh      Cl   Q.sub.23                                                                               93˜94                             86   CF.sub.3 2-NO.sub.2Ph                                                                               Cl   Q.sub.23                                                                               Oily                                    87   CF.sub.3 2-FPh       Cl   Q.sub.23                                                                               72˜73                             88   CF.sub.3 4-FPh       Cl   Q.sub.23                                                                               74˜75                             89   CF.sub.3 Ph          Cl   Q.sub.42                                                                               69˜71                             90   CF.sub.3 Ph          Cl   Q.sub.43                                                                               Oily                                    91   CF.sub.3 Ph          Cl   Q.sub.37                                                                               93˜94                             92   CF.sub.3 Ph          Cl   Q.sub.46                                                                               Oily                                    93   CF.sub.3 4-CF.sub.3Ph                                                                               Cl   Q.sub.23                                                                               61˜62                             94   CF.sub.3 4-NO.sub.2Ph                                                                               Cl   Q.sub.23                                                                               83˜84                             95   CF.sub.3 4-MeOPh     Cl   Q.sub.23                                                                               102˜104                           96   CF.sub.3 2,4-Cl.sub.2Ph                                                                             Cl   Q.sub.23                                                                               107˜108                           97   CF.sub.3 Ph          Cl   Q.sub.29                                                                               Oily                                    98   CF.sub.3 Me          NO.sub.2                                                                            Q.sub.23                                                                               73˜74                             99   Cl       Me          NO.sub.2                                                                            Q.sub.23                                                                               93˜94                             100  CF.sub.3 Ph          Cl   Q.sub.25                                                                               Oily                                    101  CF.sub.3 Ph          Cl   Q.sub.26                                                                               Oily                                    102  CF.sub.3 Ph          Cl   Q.sub.28                                                                               105˜106                           103  CF.sub.3 Me          Cl   Q.sub.23                                                                               Oily                                    104  CF.sub.3 Ph          Cl   Q.sub.18                                                                               Oily                                    105  CF.sub.3 Ph          Cl   Q.sub.49                                                                               Oily                                    106  CF.sub.3 Ph          Cl   Q.sub.50                                                                               Oily                                    107  CF.sub.3 3-CF.sub.3Ph                                                                               Cl   Q.sub.23                                                                               68˜69                             108  CF.sub.3 2-Py        Cl   Q.sub.23                                                                               105˜106                           109  CF.sub.3 Ph          Cl   Q.sub.21                                                                               120˜121                           110  CF.sub.3 Ph          Cl   Q.sub.38                                                                               133˜134                           111  CF.sub.3 Ph          Cl   Q.sub.52                                                                               Oily                                    112  CF.sub.3 Ph          Cl   Q.sub.53                                                                               Oily                                    113  CF.sub.3 Ph          Cl   Q.sub.17                                                                               Oily                                    114  CF.sub.3 Ph          Cl   Q.sub.36                                                                               130˜131                           115  Me       Ph          Cl   Q.sub.23                                                                               65˜66                             116  CF.sub.3 3-FPh       Cl   Q.sub.23                                                                               Oily                                    117  CF.sub.3 3,4-Cl.sub.2Ph                                                                             Cl   Q.sub.23                                                                               75˜76                             118  CF.sub.3 3-CF.sub.3Ph                                                                               Cl   Q.sub.23                                                                               Oily                                    119  CF.sub.3 Ph          Cl   Q.sub.33                                                                               137˜138                           120  CF.sub.3 Ph          Cl   Q.sub.34                                                                               62˜63                             121  CF.sub.3 Ph          Cl   Q.sub.35                                                                               118˜119                           122  CF.sub.3 2,5-Cl.sub.2Ph                                                                             Cl   Q.sub.23                                                                               61˜62                             123  CF.sub.3 CH.sub.2 Ph Cl   Q.sub.23                                                                               72˜73                             124  CF.sub.3 Ph          Br   Q.sub.23                                                                               59˜60                             125  CF.sub.3 Ph          Cl   Q.sub.48                                                                               86˜87                             126  CF.sub.3 Ph          Cl   Q.sub.51                                                                               84˜85                             127  CF.sub.3 Ph          Cl   Q.sub.44                                                                               Oily                                    128  CF.sub.3 Ph          Cl   Q.sub.39                                                                               89˜90                             129  CF.sub.3 Ph          Cl   Q.sub.40                                                                               85˜86                             130  CF.sub.3 Et          Cl   Q.sub.23                                                                               Oily                                    131  CF.sub.3 Et          Cl   Q.sub.31                                                                               Oily                                    132  CF.sub.3 Pr-n        Cl   Q.sub.23                                                                               Oily                                    133  CF.sub.3 3-MePh      Cl   Q.sub.19                                                                               Oily                                    134  CF.sub.3 Ph          Cl   Q.sub.30                                                                               62˜63                             135  CF.sub.3 Ph          Cl   Q.sub.22                                                                               Oily                                    136  CF.sub.3 Pr-n        Cl   Q.sub.1 Oily                                    137  CF.sub.3 Bu-tert     Cl   Q.sub.23                                                                               72˜73                             138  CF.sub.3 Ph          Cl   Q.sub.20                                                                               Oily                                    139  CF.sub.3 Pr-n        Cl   Q.sub.31                                                                               Oily                                    140  CF.sub.3 3-Cl-5-CF.sub.3 -2-Py                                                                      Cl   Q.sub.23                                                                               Oily                                    141  CF.sub.3 Ph          Cl   Q.sub.54                                                                               Oily                                    142  CF.sub.3 Ph          Cl   Q.sub.41                                                                               57˜58                             143  CF.sub.3 Pr-iso      Cl   Q.sub.23                                                                               Oily                                    144  CF.sub.3 Ph          Cl   Q.sub.45                                                                               Oily                                    145  CF.sub.3 Ph          Cl   Q.sub.16                                                                               95˜96                             146  Cl       Ph          Cl   Q.sub.23                                                                               Oily                                    147  CF.sub.3 1-NaPh      Cl   Q.sub.23                                                                               Oily                                    148  CF.sub.3 CH.sub.2 CCH                                                                               Cl   Q.sub.23                                                                               78˜79                             149  CF.sub.3 Ph          Cl   Q.sub.47                                                                               Oily                                    150  H        Me          H    Q.sub.1 77˜78                             151  CF.sub.3 Me          H    Q.sub.24                                                                               Oily                                    152  CF.sub.3 Me          H    Q.sub.1 100˜102                           153  Pr-cyc   Me          H    Q.sub.1 97˜99                             154  Me       Me          H    Q.sub.1 84˜85                             155  H        Et          H    Q.sub.1 Oily                                    156  ClF.sub.2 C                                                                             Me          H    Q.sub.1 82˜83                             157  Pr-iso   Me          H    Q.sub.1 50˜51                             158  Et       Me          H    Q.sub.1 78˜79                             159  3-ClPh   Me          H    Q.sub.6 112˜113                           160  CF.sub.3 2-Py        H    Q.sub.31                                                                               109˜110                           161  CF.sub.3 2-Py        H    Q.sub.23                                                                               125˜126                           162  Me       Ph          H    Q.sub.23                                                                               76˜77                             163  CF.sub.3 H           H    Q.sub.23                                                                               154˜156                           164  CF.sub.3 Ph          Cl   Q.sub.55                                                                               Oily                                    165  CF.sub.3 Ph          Cl   Q.sub.56                                                                               Oily                                    166  CF.sub.3 Ph          Cl   Q.sub.57                                                                               94˜95                             167  CF.sub.3 Ph          Cl   Q.sub.58                                                                               111˜112                           168  CF.sub.3 Ph          Cl   Q.sub.59                                                                               Oily                                    169  CF.sub.3 CH.sub.2 CH.sub.2 CN                                                                       H    Q.sub.1 79˜81                             170  CF.sub.3 Ph          Cl   Q.sub.60                                                                               Oily                                    171  CF.sub.3 3,5-Cl.sub.2Ph                                                                             Cl   Q.sub.23                                                                               68˜69                             172  CF.sub.3 3,5-Cl.sub.2Ph                                                                             H    Q.sub.23                                                                               108˜110                           173  CF.sub.3 Ph          Cl   Q.sub.61                                                                               Oily                                    174  CF.sub.3 CH.sub.2 CH.sub.2 CN                                                                       Cl   Q.sub.1 68˜69                             175  CF.sub.3 Hex-cyc     H    Q.sub.6 Oily                                    176  CF.sub.3 Ph          Cl   Q.sub.62                                                                               67˜69                             177  Cl       Ph          H    Q.sub.23                                                                               96˜98                             178  CF.sub.3 Hex-cyc     Cl   Q.sub.6 Oily                                    179  Ph       Ph          H    Q.sub.23                                                                               139˜140                           180  Ph       Ph          Cl   Q.sub.23                                                                               105˜106                           181  CF.sub.3 Ph          Cl   Q.sub.63                                                                               Oily                                    182  CF.sub.3 Ph          Cl   Q.sub.64                                                                               88˜90                             183  CF.sub.3 Hex-cyc     H    Q.sub.23                                                                               81˜82                             184  CF.sub.3 CH.sub.2 CHCH.sub.2                                                                        Cl   Q.sub.23                                                                               Oily                                    185  CF.sub.3 Ph          Cl   Q.sub.65                                                                               Oily                                    ______________________________________                                    

Examples of the compounds of the present invention are shown in the following Table 2, Table 3 and Table 4 along with the compounds produced in the above-mentioned examples, which, however, are not intended to restrict the scope of the present invention. The definitions of the abbreviated expressions used therein are mentioned below.

Me: methyl group

Et: ethyl group

Pr-n: normal propyl group

Pr-iso: isopropyl group

Bu-n: normal butyl group

Bu-iso: isobutyl group

Bu-sec: secondary butyl group

Bu-tert: tertiary butyl group

Pen-n: normal pentyl group

Hex-n: normal hexyl group

Pr-cyc: cyclopropyl group

Bu-cyc: cyclobutyl group

Pen-cyc: cylopentyl group

Hex-cyc: cyclohexyl group

Ph: phenyl group

                                      TABLE 2                                      __________________________________________________________________________      ##STR22##                                                                      ##STR23##                                                                      ##STR24##                                                                      ##STR25##                                                                      ##STR26##                                                                      ##STR27##                                                                      ##STR28##                                                                      ##STR29##                                                                      ##STR30##                                                                      ##STR31##                                                                      ##STR32##                                                                      ##STR33##                                                                      ##STR34##                                                                      ##STR35##                                                                      ##STR36##                                                                      ##STR37##                                                                      ##STR38##                                                                      ##STR39##                                                                      ##STR40##                                                                      ##STR41##                                                                      ##STR42##                                                                      ##STR43##                                                                      ##STR44##                                                                      ##STR45##                                                                      ##STR46##                                                                      ##STR47##                                                                      ##STR48##                                                                      ##STR49##                                                                      ##STR50##                                                                      ##STR51##                                                                      ##STR52##                                                                      ##STR53##                                                                      ##STR54##                                                                      ##STR55##                                                                      ##STR56##                                                                      ##STR57##                                                                      ##STR58##                                                                      ##STR59##                                                                      ##STR60##                                                                      ##STR61##                                                                      ##STR62##                                                                      ##STR63##                                                                      ##STR64##                                                                      ##STR65##                                                                      ##STR66##                                                                      ##STR67##                                                                      ##STR68##                                                                      ##STR69##                                                                      ##STR70##                                                                      ##STR71##                                                                      ##STR72##                                                                      ##STR73##                                                                      ##STR74##                                                                      ##STR75##                                                                      ##STR76##                                                                      ##STR77##                                                                      ##STR78##                                                                      ##STR79##                                                                      ##STR80##                                                                      ##STR81##                                                                      ##STR82##                                                                      ##STR83##                                                                      ##STR84##                                                                      ##STR85##                                                                      ##STR86##                                                                      ##STR87##                                                                      ##STR88##                                                                      ##STR89##                                                                      ##STR90##                                                                      ##STR91##                                                                      ##STR92##                                                                      ##STR93##                                                                      ##STR94##                                                                      ##STR95##                                                                      ##STR96##                                                                      ##STR97##                                                                      ##STR98##                                                                      ##STR99##                                                                      ##STR100##                                                                     ##STR101##                                                                     ##STR102##                                                                     ##STR103##                                                                     ##STR104##                                                                     ##STR105##                                                                     ##STR106##                                                                     ##STR107##                                                                     ##STR108##                                                                     ##STR109##                                                                     ##STR110##                                                                     ##STR111##                                                                     ##STR112##                                                                     ##STR113##                                                                     ##STR114##                                                                     ##STR115##                                                                     ##STR116##                                                                     ##STR117##                                                                     ##STR118##                                                                     ##STR119##                                                                     ##STR120##                                                                     ##STR121##                                                                     ##STR122##                                                                     ##STR123##                                                                     ##STR124##                                                                     ##STR125##                                                                     ##STR126##                                                                     ##STR127##                                                                     ##STR128##                                                                     ##STR129##                                                                    R.sup.1                 R.sup.2                                                __________________________________________________________________________     H                       Me                                                     H                       Et                                                     H                       Pr-n                                                   H                       Pr-iso                                                 H                       CH.sub.2 Pr-cyc                                        H                       CH.sub.2 CHCH.sub.2                                    H                       CH.sub.2 CCH                                           H                       CH.sub.2 F                                             H                       CHF.sub.2                                              H                       CF.sub.3                                               H                       CH.sub.2 OMe                                           H                       SO.sub.2 Me                                            H                       SO.sub.2 NMe.sub.2                                     H                       Ph                                                     H                       CH.sub.2 Ph                                            H                       CO.sub.2 Me                                            H                       COMe                                                   H                       CONMe.sub.2                                            H                       CH.sub.2 CO.sub.2 Me                                   H                       CHMeCO.sub.2 Et                                        H                       CH.sub.2 COMe                                          Me                      Me                                                     Me                      Et                                                     Me                      Pr-n                                                   Me                      Pr-iso                                                 Me                      CH.sub.2 Pr-cyc                                        Me                      CH.sub.2 CHCH.sub.2                                    Me                      CH.sub.2 CCH                                           Me                      CH.sub.2 F                                             Me                      CHF.sub.2                                              Me                      CF.sub.3                                               Me                      CH.sub.2 OMe                                           Me                      SO.sub.2 Me                                            Me                      SO.sub.2 NMe.sub.2                                     Me                      Ph                                                     Me                      CH.sub.2 Ph                                            Me                      CO.sub.2 Me                                            Me                      COMe                                                   Me                      CONMe.sub.2                                            Me                      CH.sub.2 CO.sub.2 Me                                   Me                      CHMeCO.sub.2 Et                                        Me                      CH.sub.2 COMe                                          Cl                      Me                                                     Cl                      Et                                                     Cl                      Pr-n                                                   Cl                      Pr-iso                                                 Cl                      Bu-n                                                   Cl                      Pen-n                                                  Cl                      Hex-n                                                  Cl                      CH.sub.2 Pr-cyc                                        Cl                      CH.sub.2 CHCH.sub.2                                    Cl                      CH.sub.2 CCH                                           Cl                      CH.sub.2 F                                             Cl                      CHF.sub.2                                              Cl                      CF.sub.3                                               Cl                      CH.sub.2 OMe                                           Cl                      SO.sub.2 Me                                            Cl                      SO.sub.2 NMe.sub.2                                     Cl                      Ph                                                     Cl                      CH.sub.2 Ph                                            Cl                      CO.sub.2 Me                                            Cl                      COMe                                                   Cl                      CONMe.sub.2                                            Cl                      CH.sub.2 CO.sub.2 Me                                   Cl                      CHMeCO.sub.2 Et                                        Cl                      CH.sub.2 COMe                                          Br                      Me                                                     Br                      Et                                                     Br                      Pr-n                                                   Br                      Pr-iso                                                 Br                      CH.sub.2 Pr-cyc                                        Br                      CH.sub.2 CHCH.sub.2                                    Br                      CH.sub.2 CCH                                           Br                      CH.sub.2 F                                             Br                      CHF.sub.2                                              Br                      CF.sub.3                                               Br                      CH.sub.2 OMe                                           Br                      SO.sub.2 Me                                            Br                      SO.sub.2 NMe.sub.2                                     Br                      Ph                                                     Br                      CH.sub.2 Ph                                            Br                      CO.sub.2 Me                                            Br                      COMe                                                   Br                      CONMe.sub.2                                            Br                      CH.sub.2 CO.sub.2 Me                                   Br                      CHMeCO.sub.2 Et                                        Br                      CH.sub.2 COMe                                          NO.sub.2                Me                                                     NO.sub.2                Et                                                     NO.sub.2                Pr-n                                                   NO.sub.2                Pr-iso                                                 NO.sub.2                CH.sub.2 Pr-cyc                                        NO.sub.2                CH.sub.2 CHCH.sub.2                                    NO.sub.2                CH.sub.2 CCH                                           NO.sub.2                CH.sub.2 F                                             NO.sub.2                CHF.sub.2                                              NO.sub.2                CF.sub.3                                               NO.sub.2                CH.sub.2 OMe                                           NO.sub.2                SO.sub.2 Me                                            NO.sub.2                SO.sub.2 NMe.sub.2                                     NO.sub.2                Ph                                                     NO.sub.2                CH.sub.2 Ph                                            NO.sub.2                CO.sub.2 Me                                            NO.sub.2                COMe                                                   NO.sub.2                CONMe.sub.2                                            NO.sub.2                CH.sub.2 CO.sub.2 Me                                   NO.sub.2                CHMeCO.sub.2 Et                                        NO.sub.2                CH.sub.2 COMe                                          CF.sub.3                Me                                                     CF.sub.3                Et                                                     CF.sub.3                Pr-n                                                   CF.sub.3                Pr-iso                                                 CF.sub.3                Bu-n                                                   CF.sub.3                Pen-n                                                  CF.sub.3                Hex-n                                                  CF.sub.3                Bu-tert                                                CF.sub.3                CH.sub.2 Pr-cyc                                        CF.sub.3                CH.sub.2 CHCH.sub.2                                    CF.sub.3                CH.sub.2 CCH                                           CF.sub.3                CH.sub.2 F                                             CF.sub.3                CHF.sub.2                                              CF.sub.3                CF.sub.3                                               CF.sub.3                CH.sub.2 OMe                                           CF.sub.3                SO.sub.2 Me                                            CF.sub.3                SO.sub.2 NMe.sub.2                                     CF.sub.3                Ph                                                     CF.sub.3                CH.sub.2 Ph                                            CF.sub.3                CO.sub.2 Me                                            CF.sub.3                COMe                                                   CF.sub.3                CONMe.sub.2                                            CF.sub.3                CH.sub.2 CO.sub.2 Me                                   CF.sub.3                CHMeCO.sub.2 Et                                        CF.sub.3                CH.sub.2 COMe                                          Et                      Me                                                     Et                      Pr-iso                                                 Et                      Et                                                     Et                      CHF.sub.2                                              Et                      CF.sub.3                                               Et                      CH.sub.2 OMe                                           Et                      Ph                                                     Et                      CH.sub.2 Ph                                            Et                      CO.sub.2 Me                                            Et                      COMe                                                   Et                      CH.sub.2 CO.sub.2 Me                                   MeO                     Me                                                     MeO                     Et                                                     MeO                     Pr-iso                                                 MeO                     CH.sub.2 OMe                                           MeO                     Ph                                                     MeS                     Me                                                     MeS                     Et                                                     MeS                     Pr-iso                                                 MeS                     CH.sub.2 OMe                                           MeS                     Ph                                                     F                       Me                                                     F                       Et                                                     F                       Pr-iso                                                 F                       CH.sub.2 OMe                                           F                       Ph                                                     Pr-n                    Me                                                     Pr-n                    Et                                                     Pr-n                    Pr-iso                                                 Pr-n                    CH.sub.2 OMe                                           Pr-n                    Ph                                                     Pr-iso                  Me                                                     Pr-iso                  Et                                                     Pr-iso                  Pr-iso                                                 Pr-iso                  CH.sub.2 OMe                                           Pr-iso                  Ph                                                     Pr-cyc                  Me                                                     Pr-cyc                  Et                                                     Pr-cyc                  Pr-iso                                                 Pr-cyc                  CH.sub.2 OMe                                           Pr-cyc                  Ph                                                     CH.sub.2 F              Me                                                     CH.sub.2 F              Et                                                     CH.sub.2 F              Pr-iso                                                 CH.sub.2 F              CH.sub.2 OMe                                           CH.sub.2 F              Ph                                                     CH.sub.2 Cl             Me                                                     CH.sub.2 Cl             Et                                                     CH.sub.2 Cl             Pr-iso                                                 CH.sub.2 Cl             CH.sub.2 OMe                                           CH.sub.2 Cl             Ph                                                     CHF.sub.2               Me                                                     CHF.sub.2               Et                                                     CHF.sub.2               Pr-iso                                                 CHF.sub.2               CH.sub.2 OMe                                           CHF.sub.2               Ph                                                     CClF.sub.2              Me                                                     CClF.sub.2              Et                                                     CClF.sub.2              Pr-iso                                                 CClF.sub.2              CH.sub.2 OMe                                           CClF.sub.2              Ph                                                     CF.sub.3 CF.sub.2       Me                                                     CF.sub.3 CF.sub.2       Et                                                     CF.sub.3 CF.sub.2       Pr-iso                                                 CF.sub.3 CF.sub.2       CH.sub.2 OMe                                           CF.sub.3 CF.sub.2       Ph                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                                             Me                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                                             Et                                                     CF.sub.3 CF.sub.2 CF.sub.2                                                                             Pr-iso                                                 CF.sub.3 CF.sub.2 CF.sub.2                                                                             CH.sub.2 OMe                                           CF.sub.3 CF.sub.2 CF.sub.2                                                                             Ph                                                     CH.sub.2 OMe            Me                                                     CH.sub.2 OMe            Et                                                     CH.sub.2 OMe            Pr-iso                                                 CH.sub.2 OMe            CH.sub.2 OMe                                           CH.sub.2 OMe            Ph                                                     CH.sub.2 SMe            Me                                                     CH.sub.2 SMe            Et                                                     CH.sub.2 SMe            Pr-iso                                                 CH.sub.2 SMe            CH.sub.2 OMe                                           CH.sub.2 SMe            Ph                                                     Ph                      Me                                                     Ph                      Et                                                     Ph                      Pr-iso                                                 Ph                      CH.sub.2 OMe                                           Ph                      Ph                                                     OCHF.sub.2              Me                                                     OCHF.sub.2              Et                                                     OCHF.sub.2              Pr-iso                                                 OCHF.sub.2              CH.sub.2 OMe                                           OCHF.sub.2              Ph                                                     Bu-n                    Me                                                     Bu-iso                  Me                                                     Bu-sec                  Me                                                     Bu-tert                 Me                                                     Pen-n                   Me                                                     Hex-n                   Me                                                     Hex-iso                 Me                                                     Bu-cyc                  Me                                                     Pen-cyc                 Me                                                     Hex-cyc                 Me                                                     CH.sub.2 Pr-cyc         Me                                                     CH.sub.2 Bu-cyc         Me                                                     CH.sub.2 Pen-cyc        Me                                                     CH.sub.2 Hex-cyc        Me                                                     CH.sub.2 CH.sub.2 Pr-cyc                                                                               Me                                                     CH.sub.2 CHCH.sub.2     Me                                                     CH.sub.2 CHCHMe         Me                                                     CH.sub.2 CH.sub.2 CHCH.sub.2                                                                           Me                                                     CH.sub.2 CCH            Me                                                     CH.sub.2 CCMe           Me                                                     OEt                     Me                                                     OPr-n                   Me                                                     OPr-iso                 Me                                                     OBu-n                   Me                                                     OBu-iso                 Me                                                     OBu-tert                Me                                                     OCH.sub.2 F             Me                                                     OCBrF.sub.2             Me                                                     OCF.sub.3               Me                                                     OCH.sub.2 CH.sub.2 Cl   Me                                                     OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                Me                                                     SEt                     Me                                                     SPr-n                   Me                                                     SPr-iso                 Me                                                     SBu-n                   Me                                                     SBu-iso                 Me                                                     SBu-tert                Me                                                     S(O)Me                  Me                                                     S(O)Et                  Me                                                     S(O)Pr-n                Me                                                     S(O)Pr-iso              Me                                                     S(O)Bu-n                Me                                                     SO.sub.2 Me             Me                                                     SO.sub.2 Et             Me                                                     SO.sub.2 Pr-n           Me                                                     SO.sub.2 Pr-iso         Me                                                     SO.sub.2 Bu-n           Me                                                     SO.sub.2 NMe.sub.2      Me                                                     SO.sub.2 NEt.sub.2      Me                                                     SO.sub.2 N(Pr-n).sub.2  Me                                                     SO.sub.2 N(Pr-iso).sub.2                                                                               Me                                                     SO.sub.2 N(Bu-n).sub.2  Me                                                     I                       Me                                                     CN                      Me                                                     NMe.sub.2               Me                                                     NEt.sub.2               Me                                                     N(Pr-n).sub.2           Me                                                     N(Pr-iso).sub.2         Me                                                     N(Bu-n).sub.2           Me                                                     CH.sub.2 Br             Me                                                     CH.sub.2 I              Me                                                     CHCl.sub.2              Me                                                     CHBr.sub.2              Me                                                     CCl.sub.3               Me                                                     CBr.sub.3               Me                                                     CF.sub.3 CH.sub.2       Me                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                                           Me                                                     ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  Me                                                     CH.sub.2 OEt            Me                                                     CH.sub.2 OPr-n          Me                                                     CH.sub.2 OBu-n          Me                                                     CH.sub.2 OBu-iso        Me                                                     CH.sub.2 OBu-sec        Me                                                     CH.sub.2 OBu-tert       Me                                                     CH.sub.2 CH.sub.2 OEt   Me                                                     CH.sub.2 CH.sub.2 OMe   Me                                                     CH.sub.2 CH.sub.2 OEt   Me                                                     CH.sub.2 CH.sub.2 OPr-n Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                         Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 OEt                                                                         Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                Me                                                     CH.sub.2 SEt            Me                                                     CH.sub.2 SPr-n          Me                                                     CH.sub.2 SBu-n          Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                                                                Me                                                     CH.sub.2 S(O)Me         Me                                                     CH.sub.2 S(O)Et         Me                                                     CH.sub.2 S(O)Pr-n       Me                                                     CH.sub.2 S(O)Bu-n       Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me                                                             Me                                                     CH.sub.2 SO.sub.2 Me    Me                                                     CH.sub.2 SO.sub.2 Et    Me                                                     CH.sub.2 SO.sub.2 Pr-n  Me                                                     CH.sub.2 SO.sub.2 Bu-n  Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me                                                        Me                                                     CH.sub.2 NMe.sub.2      Me                                                     CH.sub.2 NEt.sub.2      Me                                                     CH.sub.2 N(Pr-n).sub.2  Me                                                     CH.sub.2 N(Pr-iso).sub.2                                                                               Me                                                     CH.sub.2 N(Bu-n).sub.2  Me                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2                                                          Me                                                     2-ClPh                  Me                                                     3-ClPh                  Me                                                     4-ClPh                  Me                                                     2,4-Cl.sub.2Ph          Me                                                     2-FPh                   Me                                                     3-FPh                   Me                                                     4-FPh                   Me                                                     2-F-4-ClPh              Me                                                     2-BrPh                  Me                                                     3-BrPh                  Me                                                     4-BrPh                  Me                                                     2-MePh                  Me                                                     3-MePh                  Me                                                     4-MePh                  Me                                                     2,4-Me.sub.2Ph          Me                                                     2,6-Me.sub.2Ph          Me                                                     2-MeOPh                 Me                                                     3-MeOPh                 Me                                                     4-MeOPh                 Me                                                     2-CF.sub.3Ph            Me                                                     3-CF.sub.3Ph            Me                                                     4-CF.sub.3Ph            Me                                                     CH.sub.2 Ph             Me                                                     OCH.sub.2 Ph            Me                                                     SCH.sub.2 Ph            Me                                                     Cl                      Bu-iso                                                 Cl                      Bu-sec                                                 Cl                      Bu-tert                                                Cl                      CH.sub.2 Bu-cyc                                        Cl                      CH.sub.2 Pen-cyc                                       Cl                      CH.sub.2 Hex-cyc                                       Cl                      CH.sub.2 CH.sub.2 Pr-cyc                               Cl                      CH.sub.2 CHCHMe                                        Cl                      CH.sub.2 CH.sub.2 CHCH.sub.2                           Cl                      CH.sub.2 CCMe                                          Cl                      CH.sub.2 Cl                                            Cl                      CH.sub.2 Br                                            Cl                      CH.sub.2 I                                             Cl                      CHCl.sub.2                                             Cl                      CHBr.sub.2                                             Cl                      CCl.sub.3                                              Cl                      CBr.sub.3                                              Cl                      CClF.sub.2                                             Cl                      CF.sub.3 CH.sub.2                                      Cl                      CF.sub.3 CF.sub.2                                      Cl                      CF.sub.3 CF.sub.2 CF.sub.2                             Cl                      ClCH.sub.2 CH.sub.2 CH.sub.2                           Cl                      ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                  Cl                      SO.sub.2 Et                                            Cl                      SO.sub.2 Pr-n                                          Cl                      SO.sub.2 Pr-iso                                        Cl                      SO.sub.2 Bu-n                                          Cl                      SO.sub.2 NEt.sub.2                                     Cl                      SO.sub.2 N(Pr-n).sub.2                                 Cl                      SO.sub.2 N(Pr-iso).sub.2                               Cl                      SO.sub.2 N(Bu-n).sub.2                                 Cl                      CH.sub.2 OEt                                           Cl                      CH.sub.2 OPr-n                                         Cl                      CH.sub.2 OBu-n                                         Cl                      CH.sub.2 OBu-iso                                       Cl                      CH.sub.2 OBu-sec                                       Cl                      CH.sub.2 OBu-tert                                      Cl                      CH.sub.2 CH.sub.2 OMe                                  Cl                      CH.sub.2 CH.sub.2 OEt                                  Cl                      CH.sub.2 CH.sub.2 OPr-n                                Cl                      CH.sub.2 CH.sub.2 CH.sub.2 OMe                         Cl                      CH.sub.2 CH.sub.2 CH.sub.2 OEt                         Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                Cl                      CH.sub.2 OCH.sub.2 CH.sub.2 OMe                        Cl                      CH.sub.2 OCH.sub.2 CH.sub.2 OEt                        Cl                      CH.sub.2 SEt                                           Cl                      CH.sub.2 SPr-n                                         Cl                      CH.sub.2 SBu-n                                         Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                Cl                      CH.sub.2 S(O)Et                                        Cl                      CH.sub.2 S(O)Pr-n                                      Cl                      CH.sub.2 S(O)Bu-n                                      Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me             Cl                      CH.sub.2 SO.sub.2 Et                                   Cl                      CH.sub.2 SO.sub.2 Pr-n                                 Cl                      CH.sub.2 SO.sub.2 Bu-n                                 Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me        Cl                      CH.sub.2 NEt.sub.2                                     Cl                      CH.sub.2 N(Pr-n).sub.2                                 Cl                      CH.sub.2 N(Pr-iso).sub.2                               Cl                      CH.sub.2 N(Bu-n).sub.2                                 Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2          Cl                      2-ClPh                                                 Cl                      3-ClPh                                                 Cl                      4-ClPh                                                 Cl                      2,4-Cl.sub.2Ph                                         Cl                      2-FPh                                                  Cl                      3-FPh                                                  Cl                      4-FPh                                                  Cl                      2-F-4-ClPh                                             Cl                      2-BrPh                                                 Cl                      3-BrPh                                                 Cl                      4-BrPh                                                 Cl                      2-MePh                                                 Cl                      3-MePh                                                 Cl                      4-MePh                                                 Cl                      2,4-Me.sub.2Ph                                         Cl                      2,6-Me.sub.2Ph                                         Cl                      2-MeOPh                                                Cl                      3-MeOPh                                                Cl                      4-MeOPh                                                Cl                      2-CF.sub.3Ph                                           Cl                      3-CF.sub.3Ph                                           Cl                      4-CF.sub.3Ph                                           Cl                      CH.sub.2 Ph                                            Br                      Bu-n                                                   Br                      Bu-iso                                                 Br                      Bu-sec                                                 Br                      Bu-tert                                                Br                      Pen-n                                                  Br                      Hex-n                                                  Br                      CH.sub.2 Bu-cyc                                        Br                      CH.sub.2 Pen-cyc                                       Br                      CH.sub.2 Hex-cyc                                       Br                      CH.sub.2 CH.sub.2 Pr-cyc                               Br                      CH.sub.2 CHCHMe                                        Br                      CH.sub.2 CH.sub.2 CHCH.sub.2                           Br                      CH.sub.2 CCMe                                          Br                      CH.sub.2 Cl                                            Br                      CH.sub.2 Br                                            Br                      CH.sub.2 I                                             Br                      CHCl.sub.2                                             Br                      CHBr.sub.2                                             Br                      CCl.sub.3                                              Br                      CBr.sub.3                                              Br                      CClF.sub.2                                             Br                      CF.sub.3 CH.sub.2                                      Br                      CF.sub.3 CF.sub.2                                      Br                      CF.sub.3 CF.sub.2 CF.sub.2                             Br                      ClCH.sub.2 CH.sub.2 CH.sub.2                           Br                      ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                  Br                      SO.sub.2 Et                                            Br                      SO.sub.2 Pr-n                                          Br                      SO.sub.2 Pr-iso                                        Br                      SO.sub.2 Bu-n                                          Br                      SO.sub.2 NEt.sub.2                                     Br                      SO.sub.2 N(Pr-n).sub.2                                 Br                      SO.sub.2 N(Pr-iso).sub.2                               Br                      SO.sub.2 N(Bu-n).sub.2                                 Br                      CH.sub.2 OEt                                           Br                      CH.sub.2 OPr-n                                         Br                      CH.sub.2 OBu-n                                         Br                      CH.sub.2 OBu-iso                                       Br                      CH.sub.2 OBu-sec                                       Br                      CH.sub.2 OBu-tert                                      Br                      CH.sub.2 CH.sub.2 OMe                                  Br                      CH.sub.2 CH.sub.2 OEt                                  Br                      CH.sub.2 CH.sub.2 OPr-n                                Br                      CH.sub.2 CH.sub.2 CH.sub.2 OMe                         Br                      CH.sub.2 CH.sub.2 CH.sub.2 OEt                         Br                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                Br                      CH.sub.2 SEt                                           Br                      CH.sub.2 SPr-n                                         Br                      CH.sub.2 SBu-n                                         Br                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                Br                      CH.sub.2 S(O)Et                                        Br                      CH.sub.2 S(O)Pr-n                                      Br                      CH.sub.2 S(O)Bu-n                                      Br                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me             Br                      CH.sub.2 SO.sub.2 Et                                   Br                      CH.sub.2 SO.sub.2 Pr-n                                 Br                      CH.sub.2 SO.sub.2 Bu-n                                 Br                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me        Br                      CH.sub.2 NEt.sub.2                                     Br                      CH.sub.2 N(Pr-n).sub.2                                 Br                      CH.sub.2 N(Pr-iso).sub.2                               Br                      CH.sub.2 N(Bu-n).sub.2                                 Br                      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2          Br                      2-ClPh                                                 Br                      3-ClPh                                                 Br                      4-ClPh                                                 Br                      2,4-Cl.sub.2Ph                                         Br                      2-FPh                                                  Br                      3-FPh                                                  Br                      4-FPh                                                  Br                      2-F-4-ClPh                                             Br                      2-BrPh                                                 Br                      3-BrPh                                                 Br                      4-BrPh                                                 Br                      2-MePh                                                 Br                      3-MePh                                                 Br                      4-MePh                                                 Br                      2,4-Me.sub.2Ph                                         Br                      2,6-Me.sub.2Ph                                         Br                      2-MeOPh                                                Br                      3-MeOPh                                                Br                      4-MeOPh                                                Br                      2-CF.sub.3Ph                                           Br                      3-CF.sub.3Ph                                           Br                      4-CF.sub.3Ph                                           Br                      CH.sub.2 Ph                                            Cl                      CO.sub.2 Et                                            Cl                      CO.sub.2 Pr-n                                          Cl                      CO.sub.2 Pr-iso                                        Cl                      CO.sub.2 Bu-n                                          Cl                      COEt                                                   Cl                      COPr-n                                                 Cl                      COPr-iso                                               Cl                      COBu-n                                                 Cl                      CONHEt                                                 Cl                      CONHPr-n                                               Cl                      CONHPr-iso                                             Cl                      CONHBu-n                                               Cl                      CONEt.sub.2                                            Cl                      CON(Pr-n).sub.2                                        Cl                      CON(Pr-iso).sub.2                                      Cl                      CON(Bu-n).sub.2                                        Cl                      CH.sub.2 CO.sub.2 Et                                   Cl                      CH.sub.2 CO.sub.2 Pr-n                                 Cl                      CH.sub.2 CO.sub.2 Pr-iso                               Cl                      CH.sub.2 CO.sub.2 Bu-n                                 Cl                      CHMeCO.sub.2 Pr-n                                      Cl                      CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me                 Cl                      CH.sub.2 COEt                                          Cl                      CH.sub.2 COPr-n                                        Cl                      CH.sub.2 COPr-iso                                      Cl                      CH.sub.2 COBu-n                                        Cl                      CHMeCOMe                                               Cl                      CHMeCOEt                                               Cl                      CHMeCOPr-n                                             Cl                      CH.sub.2 CH.sub.2 CH.sub.2 COMe                        Br                      CO.sub.2 Et                                            Br                      CO.sub.2 Pr-n                                          Br                      CO.sub.2 Pr-iso                                        Br                      CO.sub.2 Bu-n                                          Br                      COEt                                                   Br                      COPr-n                                                 Br                      COPr-iso                                               Br                      COBu-n                                                 Br                      CONHEt                                                 Br                      CONHPr-n                                               Br                      CONHPr-iso                                             Br                      CONHBu-n                                               Br                      CONEt.sub.2                                            Br                      CON(Pr-n).sub.2                                        Br                      CON(Pr-iso).sub.2                                      Br                      CON(Bu-n).sub.2                                        Br                      CH.sub.2 CO.sub.2 Et                                   Br                      CH.sub.2 CO.sub.2 Pr-n                                 Br                      CH.sub.2 CO.sub.2 Pr-iso                               Br                      CH.sub.2 CO.sub.2 Bu-n                                 Br                      CHMeCO.sub.2 Pr-n                                      Br                      CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me                 Br                      CH.sub.2 COEt                                          Br                      CH.sub.2 COPr-n                                        Br                      CH.sub.2 COPr-iso                                      Br                      CH.sub.2 COBu-n                                        Br                      CHMeCOMe                                               Br                      CHMeCOEt                                               Br                      CHMeCOPr-n                                             Br                      CH.sub.2 CH.sub.2 CH.sub.2 COMe                        H                       2-ClPh                                                 H                       3-ClPh                                                 H                       4-ClPh                                                 H                       2,4-Cl.sub.2Ph                                         H                       2-FPh                                                  H                       3-FPh                                                  H                       4-FPh                                                  H                       2-F-4-ClPh                                             H                       2-BrPh                                                 H                       3-BrPh                                                 H                       4-BrPh                                                 H                       2-MePh                                                 H                       3-MePh                                                 H                       4-MePh                                                 H                       2,4-Me.sub.2Ph                                         H                       2,6-Me.sub.2Ph                                         H                       2-MeOPh                                                H                       3-MeOPh                                                H                       4-MeOPh                                                H                       2-CF.sub.3Ph                                           H                       3-CF.sub.3Ph                                           H                       4-CF.sub.3Ph                                           H                       CH.sub.2 Ph                                            Me                      2-ClPh                                                 Me                      3-ClPh                                                 Me                      4-ClPh                                                 Me                      2,4-Cl.sub.2Ph                                         Me                      2-FPh                                                  Me                      3-FPh                                                  Me                      4-FPh                                                  Me                      2-F-4-ClPh                                             Me                      2-BrPh                                                 Me                      3-BrPh                                                 Me                      4-BrPh                                                 Me                      2-MePh                                                 Me                      3-MePh                                                 Me                      4-MePh                                                 Me                      2,4-Me.sub.2Ph                                         Me                      2,6-Me.sub.2Ph                                         Me                      2-MeOPh                                                Me                      3-MeOPh                                                Me                      4-MeOPh                                                Me                      2-CF.sub.3Ph                                           Me                      3-CF.sub.3Ph                                           Me                      4-CF.sub.3Ph                                           Me                      CH.sub.2 Ph                                            CF.sub.3                2-ClPh                                                 CF.sub.3                3-ClPh                                                 CF.sub.3                4-ClPh                                                 CF.sub.3                2,4-Cl.sub.2Ph                                         CF.sub.3                2-FPh                                                  CF.sub.3                3-FPh                                                  CF.sub.3                4-FPh                                                  CF.sub.3                2-F-4-ClPh                                             CF.sub.3                2-BrPh                                                 CF.sub.3                3-BrPh                                                 CF.sub.3                4-BrPh                                                 CF.sub.3                2-MePh                                                 CF.sub.3                3-MePh                                                 CF.sub.3                4-MePh                                                 CF.sub.3                2,4-Me.sub.2Ph                                         CF.sub.3                2,6-Me.sub.2Ph                                         CF.sub.3                2-MeOPh                                                CF.sub.3                3-MeOPh                                                CF.sub.3                4-MeOPh                                                CF.sub.3                2-CF.sub.3Ph                                           CF.sub.3                3-CF.sub.3Ph                                           CF.sub.3                4-CF.sub.3Ph                                           CF.sub.3                CH.sub.2 Ph                                            3,5-Cl.sub.2Ph          Me                                                     2,6-Cl.sub.2Ph          Me                                                     2,3-Cl.sub.2Ph          Me                                                     2,4,6-Cl.sub.3Ph        Me                                                     2,3,5-Cl.sub.3Ph        Me                                                     2,3,4-Cl.sub.3Ph        Me                                                     2-NO.sub.2Ph            Me                                                     2-CNPh                  Me                                                     H                       Pr-cyc                                                 H                       Bu-cyc                                                 H                       Pen-cyc                                                H                       Hex-cyc                                                H                       3,5-Cl.sub.2Ph                                         H                       2,6-Cl.sub.2Ph                                         H                       2,3-Cl.sub.2Ph                                         H                       2,4,6-Cl.sub.3Ph                                       H                       2,3,5-Cl.sub.3Ph                                       H                       2,3,4-Cl.sub.3Ph                                       H                       2-NO.sub.2Ph                                           H                       2-CNPh                                                 H                       2-Cl-4-CF.sub.3Ph                                      H                       2,6-Cl.sub.2 -4-CF.sub.3Ph                             H                       2,5-Cl.sub.2Ph                                         H                       3,4-Cl.sub.2Ph                                         H                       2,4-(NO.sub.2).sub.2Ph                                 H                       3-NO.sub.2Ph                                           H                       4-NO.sub.2Ph                                           H                       2-Py                                                   H                       3-Py                                                   H                       4-Py                                                   H                       3-Cl-2-Py                                              H                       4-Cl-2-Py                                              H                       5-Cl-2-Py                                              H                       6-Cl-2-Py                                              H                       3-F-2-Py                                               H                       4-F-2-Py                                               H                       5-F-2-Py                                               H                       6-F-2-Py                                               H                       3-Br-2-Py                                              H                       4-Br-2-Py                                              H                       5-Br-2-Py                                              H                       6-Br-2-Py                                              H                       3-CF.sub.3 -2-Py                                       H                       4-CF.sub.3 -2-Py                                       H                       5-CF.sub.3 -2-Py                                       H                       6-CF.sub.3 -2-Py                                       H                       3-Cl-5-CF.sub.3 -2-Py                                  H                       3-Me-2-Py                                              H                       4-Me-2-Py                                              H                       5-Me-2-Py                                              H                       6-Me-2-Py                                              H                       3-NO.sub.2 -2-Py                                       H                       4-NO.sub.2 -2-Py                                       H                       5-NO.sub.2 -2-Py                                       H                       6-NO.sub.2 -2-Py                                       Me                      Pr-cyc                                                 Me                      Bu-cyc                                                 Me                      Pen-cyc                                                Me                      Hex-cyc                                                Me                      3,5-Cl.sub.2Ph                                         Me                      2,6-Cl.sub.2Ph                                         Me                      2,3-Cl.sub.2Ph                                         Me                      2,4,6-Cl.sub.3Ph                                       Me                      2,3,5-Cl.sub.3Ph                                       Me                      2,3,4-Cl.sub.3Ph                                       Me                      2-NO.sub.2Ph                                           Me                      2-CNPh                                                 Me                      2-Cl-4-CF.sub.3Ph                                      Me                      2,6-Cl.sub.2 -4-CF.sub.3Ph                             Me                      2,5-Cl.sub.2Ph                                         Me                      3,4-Cl.sub.2Ph                                         Me                      2,4-(NO.sub.2).sub.2Ph                                 Me                      3-NO.sub.2Ph                                           Me                      4-NO.sub.2Ph                                           Me                      2-Py                                                   Me                      3-Py                                                   Me                      4-Py                                                   Me                      3-Cl-2-Py                                              Me                      4-Cl-2-Py                                              Me                      5-Cl-2-Py                                              Me                      6-Cl-2-Py                                              Me                      3-F-2-Py                                               Me                      4-F-2-Py                                               Me                      5-F-2-Py                                               Me                      6-F-2-Py                                               Me                      3-Br-2-Py                                              Me                      4-Br-2-Py                                              Me                      5-Br-2-Py                                              Me                      6-Br-2-Py                                              Me                      3-CF.sub.3 -2-Py                                       Me                      4-CF.sub.3 -2-Py                                       Me                      5-CF.sub.3 -2-Py                                       Me                      6-CF.sub.3 -2-Py                                       Me                      3-Cl-5-CF.sub.3 -2-Py                                  Me                      3-Me-2-Py                                              Me                      4-Me-2-Py                                              Me                      5-Me-2-Py                                              Me                      6-Me-2-Py                                              Me                      3-NO.sub.2 -2-Py                                       Me                      4-NO.sub.2 -2-Py                                       Me                      5-NO.sub.2 -2-Py                                       Me                      6-NO.sub.2 -2-Py                                       Cl                      Pr-cyc                                                 Cl                      Bu-cyc                                                 Cl                      Pen-cyc                                                Cl                      Hex-cyc                                                Cl                      3,5-Cl.sub.2Ph                                         Cl                      2,6-Cl.sub.2Ph                                         Cl                      2,3-Cl.sub.2Ph                                         Cl                      2,4,6-Cl.sub.3Ph                                       Cl                      2,3,5-Cl.sub.3Ph                                       Cl                      2,3,4-Cl.sub.3Ph                                       Cl                      2-NO.sub.2Ph                                           Cl                      2-CNPh                                                 Cl                      2-Cl-4-CF.sub.3Ph                                      Cl                      2,6-Cl.sub.2 -4-CF.sub.3Ph                             Cl                      2,5-Cl.sub.2Ph                                         Cl                      3,4-Cl.sub.2Ph                                         Cl                      2,4-(NO.sub.2).sub.2Ph                                 Cl                      3-NO.sub.2Ph                                           Cl                      4-NO.sub.2Ph                                           Cl                      2-Py                                                   Cl                      3-Py                                                   Cl                      4-Py                                                   Cl                      3-Cl-2-Py                                              Cl                      4-Cl-2-Py                                              Cl                      5-Cl-2-Py                                              Cl                      6-Cl-2-Py                                              Cl                      3-F-2-Py                                               Cl                      4-F-2-Py                                               Cl                      5-F-2-Py                                               Cl                      6-F-2-Py                                               Cl                      3-Br-2-Py                                              Cl                      4-Br-2-Py                                              Cl                      5-Br-2-Py                                              Cl                      6-Br-2-Py                                              Cl                      3-CF.sub.3 -2-Py                                       Cl                      4-CF.sub.3 -2-Py                                       Cl                      5-CF.sub.3 -2-Py                                       Cl                      6-CF.sub.3 -2-Py                                       Cl                      3-Cl-5-CF.sub.3 -2-Py                                  Cl                      3-Me-2-Py                                              Cl                      4-Me-2-Py                                              Cl                      5-Me-2-Py                                              Cl                      6-Me-2-Py                                              Cl                      3-NO.sub.2 -2-Py                                       Cl                      4-NO.sub.2 -2-Py                                       Cl                      5-NO.sub.2 -2-Py                                       Cl                      6-NO.sub.2 -2-Py                                       Br                      Pr-cyc                                                 Br                      Bu-cyc                                                 Br                      Pen-cyc                                                Br                      Hex-cyc                                                Br                      3,5-Cl.sub.2Ph                                         Br                      2,6-Cl.sub.2Ph                                         Br                      2,3-Cl.sub.2Ph                                         Br                      2,4,6-Cl.sub.3Ph                                       Br                      2,3,5-Cl.sub.3Ph                                       Br                      2,3,4-Cl.sub.3Ph                                       Br                      2-NO.sub.2Ph                                           Br                      2-CNPh                                                 Br                      2-Cl-4-CF.sub.3Ph                                      Br                      2,6-Cl.sub.2 -4-CF.sub.3Ph                             Br                      2,5-Cl.sub.2Ph                                         Br                      3,4-Cl.sub.2Ph                                         Br                      2,4-(NO.sub.2).sub.2Ph                                 Br                      3-NO.sub.2Ph                                           Br                      4-NO.sub.2Ph                                           Br                      2-Py                                                   Br                      3-Py                                                   Br                      4-Py                                                   Br                      3-Cl-2-Py                                              Br                      4-Cl-2-Py                                              Br                      5-Cl-2-Py                                              Br                      6-Cl-2-Py                                              Br                      3-F-2-Py                                               Br                      4-F-2-Py                                               Br                      5-F-2-Py                                               Br                      6-F-2-Py                                               Br                      3-Br-2-Py                                              Br                      4-Br-2-Py                                              Br                      5-Br-2-Py                                              Br                      6-Br-2-Py                                              Br                      3-CF.sub.3 -2-Py                                       Br                      4-CF.sub.3 -2-Py                                       Br                      5-CF.sub.3 -2-Py                                       Br                      6-CF.sub.3 -2-Py                                       Br                      3-Cl-5-CF.sub.3 -2-Py                                  Br                      3-Me-2-Py                                              Br                      4-Me-2-Py                                              Br                      5-Me-2-Py                                              Br                      6-Me-2-Py                                              Br                      3-NO.sub.2 -2-Py                                       Br                      4-NO.sub.2 -2-Py                                       Br                      5-NO.sub.2 -2-Py                                       Br                      6-NO.sub.2 -2-Py                                       CF.sub.3                Pr-cyc                                                 CF.sub.3                Bu-cyc                                                 CF.sub.3                Pen-cyc                                                CF.sub.3                Hex-cyc                                                CF.sub.3                3,5-Cl.sub.2Ph                                         CF.sub.3                2,6-Cl.sub.2Ph                                         CF.sub.3                2,3-Cl.sub.2Ph                                         CF.sub.3                2,4,6-Cl.sub.3Ph                                       CF.sub.3                2,3,5-Cl.sub.3Ph                                       CF.sub.3                2,3,4-Cl.sub.3Ph                                       CF.sub.3                2-NO.sub.2Ph                                           CF.sub.3                2-CNPh                                                 CF.sub.3                3-CNPh                                                 CF.sub.3                4-CNPh                                                 CF.sub.3                CHMePh                                                 CF.sub.3                CMe.sub.2 Ph                                           CF.sub.3                2-Cl-4-CF.sub.3Ph                                      CF.sub.3                2,6-Cl.sub.2 -4-CF.sub.3Ph                             CF.sub.3                2,5-Cl.sub.2Ph                                         CF.sub.3                3,4-Cl.sub.2Ph                                         CF.sub.3                2,4-(NO.sub.2).sub.2Ph                                 CF.sub.3                3-NO.sub.2Ph                                           CF.sub.3                4-NO.sub.2Ph                                           CF.sub.3                2-Py                                                   CF.sub.3                3-Py                                                   CF.sub.3                4-Py                                                   CF.sub.3                3-Cl-2-Py                                              CF.sub.3                4-Cl-2-Py                                              CF.sub.3                5-Cl-2-Py                                              CF.sub.3                6-Cl-2-Py                                              CF.sub.3                3-F-2-Py                                               CF.sub.3                4-F-2-Py                                               CF.sub.3                5-F-2-Py                                               CF.sub.3                6-F-2-Py                                               CF.sub.3                3-Br-2-Py                                              CF.sub.3                4-Br-2-Py                                              CF.sub.3                5-Br-2-Py                                              CF.sub.3                6-Br-2-Py                                              CF.sub.3                3-CF.sub.3 -2-Py                                       CF.sub.3                4-CF.sub.3 -2-Py                                       CF.sub.3                5-CF.sub.3 -2-Py                                       CF.sub.3                6-CF.sub.3 -2-Py                                       CF.sub.3                3-Cl-5-CF.sub.3 -2-Py                                  CF.sub.3                3-Me-2-Py                                              CF.sub.3                4-Me-2-Py                                              CF.sub.3                5-Me-2-Py                                              CF.sub.3                6-Me-2-Py                                              CF.sub.3                3-NO.sub.2 -2-Py                                       CF.sub.3                4-NO.sub.2 -2-Py                                       CF.sub.3                5-NO.sub.2 -2-Py                                       CF.sub.3                6-NO.sub.2 -2-Py                                       Bu-n                    Ph                                                     Bu-iso                  Ph                                                     Bu-sec                  Ph                                                     Bu-tert                 Ph                                                     Pen-n                   Ph                                                     Hex-n                   Ph                                                     Hex-iso                 Ph                                                     Bu-cyc                  Ph                                                     Pen-cyc                 Ph                                                     Hex-cyc                 Ph                                                     CH.sub.2 Pr-cyc         Ph                                                     CH.sub.2 Bu-cyc         Ph                                                     CH.sub.2 Pen-cyc        Ph                                                     CH.sub.2 Hex-cyc        Ph                                                     CH.sub.2 CH.sub.2 Pr-cyc                                                                               Ph                                                     CH.sub.2 CHCH.sub.2     Ph                                                     CH.sub.2 CHCHPh         Ph                                                     CH.sub.2 CH.sub.2 CHCH.sub.2                                                                           Ph                                                     CH.sub.2 CCH            Ph                                                     CH.sub.2 CCMe           Ph                                                     OEt                     Ph                                                     OPr-n                   Ph                                                     OPr-iso                 Ph                                                     OBu-n                   Ph                                                     OBu-iso                 Ph                                                     OBu-tert                Ph                                                     OCH.sub.2 F             Ph                                                     OCBrF.sub.2             Ph                                                     OCF.sub.3               Ph                                                     OCH.sub.2 CH.sub.2 Cl   Ph                                                     OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                Ph                                                     SEt                     Ph                                                     SPr-n                   Ph                                                     SPr-iso                 Ph                                                     SBu-n                   Ph                                                     SBu-iso                 Ph                                                     SBu-tert                Ph                                                     S(O)Me                  Ph                                                     S(O)Et                  Ph                                                     S(O)Pr-n                Ph                                                     S(O)Pr-iso              Ph                                                     S(O)Bu-n                Ph                                                     SO.sub.2 Me             Ph                                                     SO.sub.2 Et             Ph                                                     SO.sub.2 Pr-n           Ph                                                     SO.sub.2 Pr-iso         Ph                                                     SO.sub.2 Bu-n           Ph                                                     SO.sub.2 NMe.sub.2      Ph                                                     SO.sub.2 NEt.sub.2      Ph                                                     SO.sub.2 N(Pr-n).sub.2  Ph                                                     SO.sub.2 N(Pr-iso).sub.2                                                                               Ph                                                     SO.sub.2 N(Bu-n).sub.2  Ph                                                     I                       Ph                                                     CN                      Ph                                                     NMe.sub.2               Ph                                                     NEt.sub.2               Ph                                                     N(Pr-n).sub.2           Ph                                                     N(Pr-iso).sub.2         Ph                                                     N(Bu-n).sub.2           Ph                                                     CH.sub.2 Br             Ph                                                     CH.sub.2 I              Ph                                                     CHCl.sub.2              Ph                                                     CHBr.sub.2              Ph                                                     CCl.sub.3               Ph                                                     CBr.sub.3               Ph                                                     CF.sub.3 CH.sub.2       Ph                                                     ClCH.sub.2 CH.sub.2 CH.sub.2                                                                           Ph                                                     ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  Ph                                                     CH.sub.2 OEt            Ph                                                     CH.sub.2 OPr-n          Ph                                                     CH.sub.2 OBu-n          Ph                                                     CH.sub.2 OBu-iso        Ph                                                     CH.sub.2 OBu-sec        Ph                                                     CH.sub.2 OBu-tert       Ph                                                     CH.sub.2 CH.sub.2 OEt   Ph                                                     CH.sub.2 CH.sub.2 OMe   Ph                                                     CH.sub.2 CH.sub.2 OEt   Ph                                                     CH.sub.2 CH.sub.2 OPr-n Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                         Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 OEt                                                                         Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                Ph                                                     CH.sub.2 SEt            Ph                                                     CH.sub.2 SPr-n          Ph                                                     CH.sub.2 SBu-n          Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                                                                Ph                                                     CH.sub.2 S(O)Me         Ph                                                     CH.sub.2 S(O)Et         Ph                                                     CH.sub.2 S(O)Pr-n       Ph                                                     CH.sub.2 S(O)Bu-n       Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me                                                             Ph                                                     CH.sub.2 SO.sub.2 Me    Ph                                                     CH.sub.2 SO.sub.2 Et    Ph                                                     CH.sub.2 SO.sub.2 Pr-n  Ph                                                     CH.sub.2 SO.sub.2 Bu-n  Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me                                                        Ph                                                     CH.sub.2 NMe.sub.2      Ph                                                     CH.sub.2 NEt.sub.2      Ph                                                     CH.sub.2 N(Pr-n).sub.2  Ph                                                     CH.sub.2 N(Pr-iso).sub.2                                                                               Ph                                                     CH.sub.2 N(Bu-n).sub.2  Ph                                                     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2                                                          Ph                                                     2-ClPh                  Ph                                                     3-ClPh                  Ph                                                     4-ClPh                  Ph                                                     2,4-Cl.sub.2Ph          Ph                                                     2-FPh                   Ph                                                     3-FPh                   Ph                                                     4-FPh                   Ph                                                     2-F-4-ClPh              Ph                                                     2-BrPh                  Ph                                                     3-BrPh                  Ph                                                     4-BrPh                  Ph                                                     2-MePh                  Ph                                                     3-MePh                  Ph                                                     4-MePh                  Ph                                                     2,4-Me.sub.2Ph          Ph                                                     2,6-Me.sub.2Ph          Ph                                                     2-MeOPh                 Ph                                                     3-MeOPh                 Ph                                                     4-MeOPh                 Ph                                                     2-CF.sub.3Ph            Ph                                                     3-CF.sub.3Ph            Ph                                                     4-CF.sub.3Ph            Ph                                                     CH.sub.2 Ph             Ph                                                     OCH.sub.2 Ph            Ph                                                     SCH.sub.2 Ph            Ph                                                     Bu-n                    2-Py                                                   Bu-iso                  2-Py                                                   Bu-sec                  2-Py                                                   Bu-tert                 2-Py                                                   Pen-n                   2-Py                                                   Hex-n                   2-Py                                                   Hex-iso                 2-Py                                                   Bu-cyc                  2-Py                                                   Pen-cyc                 2-Py                                                   Hex-cyc                 2-Py                                                   CH.sub.2 Pr-cyc         2-Py                                                   CH.sub.2 Bu-cyc         2-Py                                                   CH.sub.2 Pen-cyc        2-Py                                                   CH.sub.2 Hex-cyc        2-Py                                                   CH.sub.2 CH.sub.2 Pr-cyc                                                                               2-Py                                                   CH.sub.2 CHCH.sub.2     2-Py                                                   CH.sub.2 CHCHMe         2-Py                                                   CH.sub.2 CH.sub.2 CHCH.sub.2                                                                           2-Py                                                   CH.sub.2 CCH            2-Py                                                   CH.sub.2 CCMe           2-Py                                                   OEt                     2-Py                                                   OPr-n                   2-Py                                                   OPr-iso                 2-Py                                                   OBu-n                   2-Py                                                   OBu-iso                 2-Py                                                   OBu-tert                2-Py                                                   OCH.sub.2 F             2-Py                                                   OCBrF.sub.2             2-Py                                                   OCF.sub.3               2-Py                                                   OCH.sub.2 CH.sub.2 Cl   2-Py                                                   OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                2-Py                                                   SEt                     2-Py                                                   SPr-n                   2-Py                                                   SPr-iso                 2-Py                                                   SBu-n                   2-Py                                                   SBu-iso                 2-Py                                                   SBu-tert                2-Py                                                   S(O)Me                  2-Py                                                   S(O)Et                  2-Py                                                   S(O)Pr-n                2-Py                                                   S(O)Pr-iso              2-Py                                                   S(O)Bu-n                2-Py                                                   SO.sub.2 Me             2-Py                                                   SO.sub.2 Et             2-Py                                                   SO.sub.2 Pr-n           2-Py                                                   SO.sub.2 Pr-iso         2-Py                                                   SO.sub.2 Bu-n           2-Py                                                   SO.sub.2 NMe.sub.2      2-Py                                                   SO.sub.2 NEt.sub.2      2-Py                                                   SO.sub.2 N(Pr-n).sub.2  2-Py                                                   SO.sub.2 N(Pr-iso).sub.2                                                                               2-Py                                                   SO.sub.2 N(Bu-n).sub.2  2-Py                                                   I                       2-Py                                                   CN                      2-Py                                                   NMe.sub.2               2-Py                                                   NEt.sub.2               2-Py                                                   N(Pr-n).sub.2           2-Py                                                   N(Pr-iso).sub.2         2-Py                                                   N(Bu-n).sub.2           2-Py                                                   CH.sub.2 Br             2-Py                                                   CH.sub.2 I              2-Py                                                   CHCl.sub.2              2-Py                                                   CHBr.sub.2              2-Py                                                   CCl.sub.3               2-Py                                                   CBr.sub.3               2-Py                                                   CF.sub.3 CH.sub.2       2-Py                                                   ClCH.sub.2 CH.sub.2 CH.sub.2                                                                           2-Py                                                   ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                                  2-Py                                                   CH.sub.2 OEt            2-Py                                                   CH.sub.2 OPr-n          2-Py                                                   CH.sub.2 OBu-n          2-Py                                                   CH.sub.2 OBu-iso        2-Py                                                   CH.sub.2 OBu-sec        2-Py                                                   CH.sub.2 OBu-tert       2-Py                                                   CH.sub.2 CH.sub.2 OEt   2-Py                                                   CH.sub.2 CH.sub.2 OMe   2-Py                                                   CH.sub.2 CH.sub.2 OEt   2-Py                                                   CH.sub.2 CH.sub.2 OPr-n 2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                         2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 OEt                                                                         2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                2-Py                                                   CH.sub.2 SEt            2-Py                                                   CH.sub.2 SPr-n          2-Py                                                   CH.sub.2 SBu-n          2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                                                                2-Py                                                   CH.sub.2 S(O)Me         2-Py                                                   CH.sub.2 S(O)Et         2-Py                                                   CH.sub.2 S(O)Pr-n       2-Py                                                   CH.sub.2 S(O)Bu-n       2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me                                                             2-Py                                                   CH.sub.2 SO.sub.2 Me    2-Py                                                   CH.sub.2 SO.sub.2 Et    2-Py                                                   CH.sub.2 SO.sub.2 Pr-n  2-Py                                                   CH.sub.2 SO.sub.2 Bu-n  2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me                                                        2-Py                                                   CH.sub.2 NMe.sub.2      2-Py                                                   CH.sub.2 NEt.sub.2      2-Py                                                   CH.sub.2 N(Pr-n).sub.2  2-Py                                                   CH.sub.2 N(Pr-iso).sub.2                                                                               2-Py                                                   CH.sub.2 N(Bu-n).sub.2  2-Py                                                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2                                                          2-Py                                                   2-ClPh                  2-Py                                                   3-ClPh                  2-Py                                                   4-ClPh                  2-Py                                                   2,4-Cl.sub.2Ph          2-Py                                                   2-FPh                   2-Py                                                   3-FPh                   2-Py                                                   4-FPh                   2-Py                                                   2-F-4-ClPh              2-Py                                                   2-BrPh                  2-Py                                                   3-BrPh                  2-Py                                                   4-BrPh                  2-Py                                                   2-MePh                  2-Py                                                   3-MePh                  2-Py                                                   4-MePh                  2-Py                                                   2,4-Me.sub.2Ph          2-Py                                                   2,6-Me.sub.2Ph          2-Py                                                   2-MeOPh                 2-Py                                                   3-MeOPh                 2-Py                                                   4-MeOPh                 2-Py                                                   2-CF.sub.3Ph            2-Py                                                   3-CF.sub.3Ph            2-Py                                                   4-CF.sub.3Ph            2-Py                                                   CH.sub.2 Ph             2-Py                                                   OCH.sub.2 Ph            2-Py                                                   SCH.sub.2 Ph            2-Py                                                   Cl                      Bu-tert                                                Cl                      Bu-iso                                                 Cl                      Bu-sec                                                 Cl                      3-CNPh                                                 Cl                      4-CNPh                                                 Cl                      CHMePh                                                 Cl                      CMe.sub.2 Ph                                           Br                      3-CNPh                                                 Br                      4-CNPh                                                 Br                      CHMePh                                                 Br                      CMe.sub.2 Ph                                           CF.sub.3                Bu-iso                                                 CF.sub.3                Bu-sec                                                 CF.sub.3                CH.sub.2 Bu-cyc                                        CF.sub.3                CH.sub.2 Pen-cyc                                       CF.sub.3                CH.sub.2 Hex-cyc                                       CF.sub.3                CH.sub.2 CH.sub.2 Pr-cyc                               CF.sub.3                CH.sub.2 CHCHMe                                        CF.sub.3                CH.sub.2 CH.sub.2 CHCH.sub.2                           CF.sub.3                CH.sub.2 CCMe                                          CF.sub.3                CH.sub.2 Cl                                            CF.sub.3                CH.sub.2 Br                                            CF.sub.3                CH.sub.2 I                                             CF.sub.3                CHCl.sub.2                                             CF.sub.3                CHBr.sub.2                                             CF.sub.3                CCl.sub.3                                              CF.sub.3                CBr.sub.3                                              CF.sub.3                CClF.sub.2                                             CF.sub.3                CF.sub.3 CH.sub.2                                      CF.sub.3                CF.sub.3 CF.sub.2                                      CF.sub.3                CF.sub.3 CF.sub.2 CF.sub.2                             CF.sub.3                ClCH.sub.2 CH.sub.2 CH.sub.2                           CF.sub.3                ClCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                  CF.sub.3                SO.sub.2 Et                                            CF.sub.3                SO.sub.2 Pr-n                                          CF.sub.3                SO.sub.2 Pr-iso                                        CF.sub.3                SO.sub.2 Bu-n                                          CF.sub.3                SO.sub.2 NEt.sub.2                                     CF.sub.3                SO.sub.2 N(Pr-n).sub.2                                 CF.sub.3                SO.sub.2 N(Pr-iso).sub.2                               CF.sub.3                SO.sub.2 N(Bu-n).sub.2                                 CF.sub.3                CH.sub.2 OEt                                           CF.sub.3                CH.sub.2 OPr-n                                         CF.sub.3                CH.sub.2 OBu-n                                         CF.sub.3                CH.sub.2 OBu-iso                                       CF.sub.3                CH.sub.2 OBu-sec                                       CF.sub.3                CH.sub.2 OBu-tert                                      CF.sub.3                CH.sub.2 CH.sub.2 OMe                                  CF.sub.3                CH.sub.2 CH.sub.2 OEt                                  CF.sub.3                CH.sub.2 CH.sub.2 OPr-n                                CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 OMe                         CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 OEt                         CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                CF.sub.3                CH.sub.2 OCH.sub.2 CH.sub.2 OMe                        CF.sub.3                CH.sub.2 OCH.sub.2 CH.sub.2 OEt                        CF.sub.3                CH.sub.2 SEt                                           CF.sub.3                CH.sub.2 SPr-n                                         CF.sub.3                CH.sub.2 SBu-n                                         CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SMe                CF.sub.3                CH.sub.2 S(O)Et                                        CF.sub.3                CH.sub.2 S(O)Pr-n                                      CF.sub.3                CH.sub.2 S(O)Bu-n                                      CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 S(O)Me             CF.sub.3                CH.sub.2 SO.sub.2 Et                                   CF.sub.3                CH.sub.2 SO.sub.2 Pr-n                                 CF.sub.3                CH.sub.2 SO.sub.2 Bu-n                                 CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 Me        CF.sub.3                CH.sub.2 NEt.sub.2                                     CF.sub.3                CH.sub.2 N(Pr-n).sub.2                                 CF.sub.3                CH.sub.2 N(Pr-iso).sub.2                               CF.sub.3                CH.sub.2 N(Bu-n).sub.2                                 CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 NMe.sub.2          CF.sub.3                CO.sub.2 Et                                            CF.sub.3                CO.sub.2 Pr-n                                          CF.sub.3                CO.sub.2 Pr-iso                                        CF.sub.3                CO.sub.2 Bu-n                                          CF.sub.3                COEt                                                   CF.sub.3                COPr-n                                                 CF.sub.3                COPr-iso                                               CF.sub.3                COBu-n                                                 CF.sub.3                CONHEt                                                 CF.sub.3                CONHPr-n                                               CF.sub.3                CONHPr-iso                                             CF.sub.3                CONHBu-n                                               CF.sub.3                CONEt.sub.2                                            CF.sub.3                CON(Pr-n).sub.2                                        CF.sub.3                CON(Pr-iso).sub.2                                      CF.sub.3                CON(Bu-n).sub.2                                        CF.sub.3                CH.sub.2 CO.sub.2 Et                                   CF.sub.3                CH.sub.2 CO.sub.2 Pr-n                                 CF.sub.3                CH.sub.2 CO.sub.2 Pr-iso                               CF.sub.3                CH.sub.2 CO.sub.2 Bu-n                                 CF.sub.3                CHMeCO.sub.2 Pr-n                                      CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me                 CF.sub.3                CH.sub.2 COEt                                          CF.sub.3                CH.sub.2 COPr-n                                        CF.sub.3                CH.sub.2 COPr-iso                                      CF.sub.3                CH.sub.2 COBu-n                                        CF.sub.3                CHMeCOMe                                               CF.sub.3                CHMeCOEt                                               CF.sub.3                CHMeCOPr-n                                             CF.sub.3                CH.sub.2 CH.sub.2 CH.sub.2 COMe                        __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR130##                                                                     ##STR131##                                                                     ##STR132##                                                                     ##STR133##                                                                     ##STR134##                                                                     ##STR135##                                                                     ##STR136##                                                                     ##STR137##                                                                     ##STR138##                                                                     ##STR139##                                                                     ##STR140##                                                                     ##STR141##                                                                    R.sup.4              R.sup.5                                                   __________________________________________________________________________     Et                   Ph                                                        Pr-n                 Ph                                                        Pr-iso               Ph                                                        Bu-n                 Ph                                                        Bu-iso               Ph                                                        Bu-sec               Ph                                                        Bu-tert              Ph                                                        Pen-n                Ph                                                        Hex-n                Ph                                                        Hex-iso              Ph                                                        Pr-cyc               Ph                                                        Bu-cyc               Ph                                                        Pen-cyc              Ph                                                        Hex-cyc              Ph                                                        CH.sub.2 Pr-cyc      Ph                                                        CH.sub.2 Bu-cyc      Ph                                                        CH.sub.2 Pen-cyc     Ph                                                        CH.sub.2 Hex-cyc     Ph                                                        CH.sub.2 CH.sub.2 Pr-cyc                                                                            Ph                                                        CH.sub.2 CHCH.sub.2  Ph                                                        CH.sub.2 CHCHMe      Ph                                                        CH.sub.2 CH.sub.2 CHCH.sub.2                                                                        Ph                                                        CH.sub.2 CCH         Ph                                                        CH.sub.2 CCMe        Ph                                                        OMe                  Ph                                                        OEt                  Ph                                                        OPr-n                Ph                                                        OPr-iso              Ph                                                        OBu-n                Ph                                                        OBu-iso              Ph                                                        OBu-tert             Ph                                                        SO.sub.2 Me          Ph                                                        SO.sub.2 Et          Ph                                                        SO.sub.2 Pr-n        Ph                                                        SO.sub.2 Pr-iso      Ph                                                        SO.sub.2 Bu-n        Ph                                                        CH.sub.2 OMe         Ph                                                        CH.sub.2 OEt         Ph                                                        CH.sub.2 OPr-n       Ph                                                        CH.sub.2 OBu-n       Ph                                                        CH.sub.2 OBu-iso     Ph                                                        CH.sub.2 OBu-sec     Ph                                                        CH.sub.2 OBu-tert    Ph                                                        CH.sub.2 CH.sub.2 OMe                                                                               Ph                                                        CH.sub.2 CH.sub.2 OEt                                                                               Ph                                                        CH.sub.2 CH.sub.2 OPr-n                                                                             Ph                                                        CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                                      Ph                                                        CH.sub.2 CH.sub.2 CH.sub.2 OEt                                                                      Ph                                                        CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                                                             Ph                                                        CH.sub.2 CH.sub.2 OMe                                                                               CH.sub.2 CH.sub.2 OMe                                     Me                   3-ClPh                                                    Me                   4-ClPh                                                    Me                   2,4-Cl.sub.2Ph                                            Me                   3,5-Cl.sub.2Ph                                            Me                   2,3-Cl.sub.2Ph                                            Me                   2,5-Cl.sub.2Ph                                            Me                   3-FPh                                                     Me                   4-FPh                                                     Me                   2-F-4-Cl                                                  Me                   2-BrPh                                                    Me                   3-BrPh                                                    Me                   4-BrPh                                                    Me                   3-MePh                                                    Me                   4-MePh                                                    Me                   2,4-Me.sub.2Ph                                            Me                   3,5-Me.sub.2Ph                                            Me                   2,6-Me.sub.2Ph                                            Me                   2,3-Me.sub.2Ph                                            Me                   2,5-Me.sub.2Ph                                            Me                   2-MeOPh                                                   Me                   3-MeOPh                                                   Me                   4-MeOPh                                                   Me                   2-CF.sub.3Ph                                              Me                   3-CF.sub.3Ph                                              Me                   4-CF.sub.3Ph                                              Me                   CH.sub.2 Ph                                               Et                   Et                                                        Pr-n                 Pr-n                                                      Pr-iso               Pr-iso                                                    Bu-n                 Bu-n                                                      H                    Ph                                                        Me                   OMe                                                       Me                   OEt                                                       Me                   OBu-n                                                     Me                   2,4,6-Cl.sub.3Ph                                          Me                   2,3,5-Cl.sub.3Ph                                          Me                   2,3,4-Cl.sub.3Ph                                          Me                   2-NO.sub.2Ph                                              Me                   2-CNPh                                                    Me                   Me                                                        Me                   Et                                                        Me                   Pr-iso                                                    Me                   Bu-iso                                                    Me                   Bu-sec                                                    Et                   Pr-n                                                      Et                   Pr-iso                                                    Et                   Bu-n                                                      Et                   Bu-iso                                                    Et                   Bu-sec                                                    Pr-n                 Pr-iso                                                    Pr-n                 Bu-n                                                      Pr-n                 Bu-iso                                                    Pr-n                 Bu-sec                                                    Bu-n                 Bu-iso                                                    Bu-n                 Bu-sec                                                    Bu-iso               Bu-iso                                                    Bu-iso               Bu-sec                                                    Bu-sec               Bu-sec                                                    OMe                  CH.sub.2 CHCH.sub.2                                       OMe                  CH.sub.2 CHCH                                             OEt                  CH.sub.2 CHCH.sub.2                                       OEt                  CH.sub.2 CHCH                                             Me                   H                                                         Me                   Bu-tert                                                   Me                   Hex-iso                                                   Me                   Pr-cyc                                                    Me                   Bu-cyc                                                    Me                   CHMeCHMe.sub.2                                            Me                   Pen-cyc                                                   Me                   Hex-cyc                                                   Me                   CH.sub.2 Pr-cyc                                           Me                   CH.sub.2 Bu-cyc                                           Me                   CH.sub.2 Pen-cyc                                          Me                   CH.sub.2 Hex-cyc                                          Me                   CH.sub.2 CH.sub.2 Pr-cyc                                  Me                   CH.sub.2 CHCHMe                                           Me                   CH.sub.2 CH.sub.2 CHCH.sub.2                              Me                   CH.sub.2 CCMe                                             Me                   CH.sub.2 OMe                                              Me                   CH.sub.2 OEt                                              Me                   CH.sub.2 OPr-n                                            Me                   CH.sub.2 OBu-n                                            Me                   CH.sub.2 OBu-iso                                          Me                   CH.sub.2 OBu-sec                                          Me                   CH.sub.2 OBu-tert                                         Me                   CH.sub.2 CH.sub.2 OMe                                     Me                   CH.sub.2 CH.sub.2 OEt                                     Me                   CH.sub.2 CH.sub.2 OPr-n                                   Me                   CH.sub.2 CH.sub.2 CH.sub.2 OMe                            Me                   CH.sub.2 CH.sub.2 CH.sub.2 OEt                            Me                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                   Me                   OPr-n                                                     Me                   OPr-iso                                                   Me                   OBu-iso                                                   Me                   OBu-tert                                                  Me                   SO.sub.2 Me                                               Me                   SO.sub.2 Et                                               Me                   SO.sub.2 Pr-n                                             Me                   SO.sub.2 Pr-iso                                           Me                   SO.sub.2 Bu-n                                             Me                   COMe                                                      Me                   COEt                                                      Me                   COPr-n                                                    Me                   COPr-iso                                                  Me                   COBu-n                                                    Me                   CO.sub.2 Me                                               Me                   CO.sub.2 Et                                               Me                   CO.sub.2 Pr-n                                             Me                   CO.sub.2 Pr-iso                                           Me                   CO.sub.2 Bu-n                                             Me                   CH.sub.2 CO.sub.2 Me                                      Me                   CH.sub.2 CO.sub.2 Et                                      Me                   CH.sub.2 CO.sub.2 Pr-n                                    Me                   CH.sub.2 CO.sub.2 Bu-n                                    Me                   CHMeCO.sub.2 Me                                           Me                   CHMeCO.sub.2 Et                                           Me                   CH.sub.2 CH.sub.2 CO.sub.2 Me                             Me                   CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me                    Me                   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me           Me                   CH(Pr-iso)CO.sub.2 Me                                     Me                   CH(Bu-sec)CO.sub.2 Me                                     Me                   CH(Bu-iso)CO.sub.2 Me                                     Me                   CH(CH.sub.2 Ph)CO.sub.2 Me                                Me                   CH.sub.2 CH.sub.2 CN                                      Me                   1-Naph                                                    Me                   2-Naph                                                    Me                   CH.sub.2 -1-Naph                                          Me                   CH.sub.2 -2-Naph                                          Me                   CH.sub.2 Ph                                               Me                   CHMePh                                                    Me                   CMe.sub.2 Ph                                              Me                   CH.sub.2 -2-ClPh                                          Me                   CH.sub.2 -3-ClPh                                          Me                   CH.sub.2 -4-ClPh                                          Me                   2-Py                                                      Me                   6-MeO-2-Py                                                Me                   3-MeO-2-Py                                                Me                   6-Cl-2-Py                                                 Me                   6-F-2-Py                                                  Me                   5-CF.sub.3 -2-Py                                          Me                   3-Cl-5-CF.sub.3 -2-Py                                     Me                   3-Py                                                      Me                   4-Py                                                      Me                   CH.sub.2 -5-Cl-2-Py                                       Me                   CH.sub.2 -6-Cl-3-Py                                       H                    H                                                         H                    Et                                                        H                    Pr-n                                                      H                    Pr-iso                                                    H                    Bu-n                                                      H                    Bu-iso                                                    H                    Bu-sec                                                    H                    Bu-tert                                                   H                    CHMeCHMe.sub.2                                            H                    Pen-n                                                     H                    Hex-n                                                     H                    Hex-iso                                                   H                    Pr-cyc                                                    H                    Bu-cyc                                                    H                    Pen-cyc                                                   H                    Hex-cyc                                                   H                    CH.sub.2 Pr-cyc                                           H                    CH.sub.2 Bu-cyc                                           H                    CH.sub.2 Pen-cyc                                          H                    CH.sub.2 Hex-cyc                                          H                    CH.sub.2 CH.sub.2 Pr-cyc                                  H                    CH.sub.2 CHCH.sub.2                                       H                    CH.sub.2 CHCHMe                                           H                    CH.sub.2 CH.sub.2 CHCH.sub.2                              H                    CH.sub.2 CCH                                              H                    CH.sub.2 CCMe                                             H                    CH.sub.2 OMe                                              H                    CH.sub.2 OEt                                              H                    CH.sub.2 OPr-n                                            H                    CH.sub.2 OBu-n                                            H                    CH.sub.2 OBu-iso                                          H                    CH.sub.2 OBu-sec                                          H                    CH.sub.2 OBu-tert                                         H                    CH.sub.2 CH.sub.2 OMe                                     H                    CH.sub.2 CH.sub.2 OEt                                     H                    CH.sub.2 CH.sub.2 OPr-n                                   H                    CH.sub.2 CH.sub.2 CH.sub.2 OMe                            H                    CH.sub.2 CH.sub.2 CH.sub.2 OEt                            H                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OMe                   H                    2-ClPh                                                    H                    3-ClPh                                                    H                    4-ClPh                                                    H                    2,4-Cl.sub.2Ph                                            H                    3,5-Cl.sub.2Ph                                            H                    2,6-Cl.sub.2Ph                                            H                    2,3-Cl.sub.2Ph                                            H                    2,5-Cl.sub.2Ph                                            H                    2-FPh                                                     H                    3-FPh                                                     H                    4-FPh                                                     H                    2-F-4-ClPh                                                H                    2-BrPh                                                    H                    3-BrPh                                                    H                    4-BrPh                                                    H                    2-MePh                                                    H                    3-MePh                                                    H                    4-MePh                                                    H                    2,4-Me.sub.2Ph                                            H                    3,5-Me.sub.2Ph                                            H                    2,6-Me.sub.2Ph                                            H                    2,3-Me.sub.2Ph                                            H                    2,5-Me.sub.2Ph                                            H                    2-MeOPh                                                   H                    3-MeOPh                                                   H                    4-MeOPh                                                   H                    2-CF.sub.3Ph                                              H                    3-CF.sub.3Ph                                              H                    4-CF.sub.3Ph                                              H                    2,4,6-Cl.sub.3Ph                                          H                    2,3,5-Cl.sub.3Ph                                          H                    2,3,4-Cl.sub.3Ph                                          H                    2-NO.sub.2Ph                                              H                    2-CNPh                                                    H                    CH.sub.2 Ph                                               H                    OMe                                                       H                    OEt                                                       H                    OPr-n                                                     H                    OPr-iso                                                   H                    OBu-n                                                     H                    OBu-iso                                                   H                    OBu-tert                                                  H                    SO.sub.2 Me                                               H                    SO.sub.2 Et                                               H                    SO.sub.2 Pr-n                                             H                    SO.sub.2 Pr-iso                                           H                    SO.sub.2 Bu-n                                             H                    COMe                                                      H                    COEt                                                      H                    COPr-n                                                    H                    COPr-iso                                                  H                    COBu-n                                                    H                    CO.sub.2 Me                                               H                    CO.sub.2 Et                                               H                    CO.sub.2 Pr-n                                             H                    CO.sub.2 Pr-iso                                           H                    CO.sub.2 Bu-n                                             H                    CH.sub.2 CO.sub.2 Me                                      H                    CH.sub.2 CO.sub.2 Et                                      H                    CH.sub.2 CO.sub.2 Pr-n                                    H                    CH.sub.2 CO.sub.2 Bu-n                                    H                    CHMeCO.sub.2 Me                                           H                    CHMeCO.sub.2 Et                                           H                    CH.sub.2 CH.sub.2 CO.sub.2 Me                             H                    CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me                    H                    CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CO.sub.2 Me           H                    CH(Pr-iso)CO.sub.2 Me                                     H                    CH(Bu-sec)CO.sub.2 Me                                     H                    CH(Bu-iso)CO.sub.2 Me                                     H                    CH(CH.sub.2 Ph)CO.sub.2 Me                                H                    CH.sub.2 CH.sub.2 CN                                      H                    1-Naph                                                    H                    2-Naph                                                    H                    CH.sub.2 -1-Naph                                          H                    CH.sub.2 -2-Naph                                          H                    CH.sub.2 Ph                                               H                    CHMePh                                                    H                    CMe.sub.2 Ph                                              H                    CH.sub.2 -2-ClPh                                          H                    CH.sub.2 -3-ClPh                                          H                    CH.sub.2 -4-ClPh                                          H                    2-Py                                                      H                    6-MeO-2-Py                                                H                    3-MeO-2-Py                                                H                    6-Cl-2-Py                                                 H                    6-F-2-Py                                                  H                    5-CF.sub.3 -2-Py                                          H                    3-Cl-5-CF.sub.3 -2-Py                                     H                    3-Py                                                      H                    4-Py                                                      H                    CH.sub.2 -5-Cl-2-Py                                       H                    CH.sub.2 -6-Cl-3-Py                                       __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR142##                                                                     ##STR143##                                                                     ##STR144##                                                                     ##STR145##                                                                     ##STR146##                                                                     ##STR147##                                                                     ##STR148##                                                                     ##STR149##                                                                     ##STR150##                                                                     ##STR151##                                                                     ##STR152##                                                                     ##STR153##                                                                    __________________________________________________________________________

In Table 4, NR⁴ R⁵ represents: ##STR154##

The dose of the compounds of the present invention to be applied to agricultural land, etc. varies, depending on the scene to which they are applied, the time when they are applied, the method by which they are applied, the weeds which shall be terminated by them and the crop plants which they shall protect from harmful weeds, etc. In general, it is suitably from 0.001 to 50 kg/ha (hectare) or so, preferably from 0.01 to 10 kg/ha or so, as the amount of the active ingredient.

If desired, the compounds of the present invention may be combined with other herbicides, various insecticides, fungicides, plant growth regulators, synergism agents, etc. at the time of formulations or applications.

In particular, they are preferably combined with other herbicides, whereby the dose of them to be used may be reduced so that the costs of the herbicidal products containing them may be lowered and, additionally, their herbicidal spectra may be broadened due to the synergistic effect of the added chemicals so that the combined products may have a higher herbicidal effect. To prepare such combined products, plural known herbicides may be combined with the compounds of the present invention.

As herbicides which may be combined with the compounds of the present invention, for example, mentioned are the compounds described in Farm Chemicals Handbook (1990).

As chemicals which are preferably combined with the compounds of the present invention, for example, mentioned are pyrazosulfuron ethyl (common name), bensulfuron methyl (common name), cinosulfuron (common name) and imazosulfuron (common name).

In addition to these, the following chemicals may also be combined with the compounds of the present invention:

Pretilachlor (common name), esprocarb (common name), pyrazolate (common name), pyrazoxyfen (common name), benzofenap (common name), dymron (common name), bromobutide (common name), naproanilide (common name), clomeprop (common name), CNP (common name), chlomethoxynil (common name), bifenox (common name), oxadiazon (common name), mefenacet (common name), butachlor (common name), butenachlor (common name), dithiopyr (common name), benfuresate (common name), pyributicarb (common name), benthiocarb (common name), dimepiperate (common name), molinate (common name), butamifos (common name), quinclorac (common name), cinmethylin (common name), simetryn (common name), SAP (bensulide - common name), dimethametryn (common name), MCPA, MCPB, 2',3'-dichloro-4-ethoxymethoxybenzanilide (HW-52 as test name), 1-(2-chlorobenzyl)-3-(α,α-dimethylbenzyl)urea (JC-940 as test name), N-[2'-(3'-methoxy)-thienylmethyl]-N-chloroacetyl-2,6-dimethylanilide (NSK-850 as test name), etc.

Where the compounds of the present invention are used as herbicide, in general, they may be mixed with pertinent carriers, for example, solid carriers such as clay, talc, bentonite, diatomaceous earth, white carbon, etc. or liquid carriers such as water, alcohols (e.g., isopropanol, butanol, benzyl alcohol, furfuryl-alcohol, etc.), aromatic hydrocarbons (e.g., toluene, xylene, etc.), ethers (e.g., anisole, etc.), ketones (e.g., cyclohexanone, isophorone, etc.), esters (e.g., butyl acetate, etc.), acid amides (e.g., N-methylpyrrolidone, etc.) or halogenated .hydrocarbons (e.g., chlorobenzene, etc.). If desired, they may be prepared into various practical formulations, including liquid formulation, emulsifiable concentrate, wettable powder, dry flowable powder, flowable liquid, dust, granule, etc., optionally along with surfactant, emulsifier, dispersing agent, penetration promoter, adhesion promoter, tackifier, anti-freezing agent, anti-caking agent, stabilizer, etc.

Where the compounds of the present invention are formulated into herbicidal granules to be applied to paddy fields, for example, usable are kaolinite, montmorillonite, diatomaceous earth, bentonite, talc, clay, calcium carbonate, calcium sulfate, ammonium sulfate, etc., as the solid carriers, and alkylbenzenesulfonates, polyoxyethylene alkylaryl ethers, ligninesulfonates, alkylsulfosuccinates, polyoxyethylene fatty acid esters, naphthalenesulfonates, polyoxyethylene alkylaryl ether sulfates, alkylamine salts, tripolyphosphates, etc., as the surfactants. The content of these surfactants in the herbicidal granules is not specifically defined but is, in general, desirably within the range of from 0.05 to 20 parts by weight relative to 100 parts by weight of the granules. If desired, the granules may contain a decomposition inhibitor such as epoxidated soybean oil, etc.

Next, examples of formulations of herbicidal products containing the compounds of the present invention are mentioned below, which, however, are not limitative. In the following examples, all "parts" are by weight.

    ______________________________________                                         Wettable Powder:                                                               ______________________________________                                         Compound of this invention                                                                           5 to 80  pts.                                            Solid carrier         10 to 85 pts.                                            Surfactant            1 to 10  pts.                                            Others                1 to 5   pts.                                            ______________________________________                                    

As others, for example, mentioned are anti-caking agent, etc.

    ______________________________________                                         Emulsifiable concentrate:                                                      Compound of this invention                                                                           1 to 30  pts.                                            Liquid carrier        30 to 95 pts.                                            Surfactant            5 to 15  pts.                                            Flowable Liquid:                                                               Compound of this invention                                                                           5 to 70  pts.                                            Liquid Carrier        15 to 65 pts.                                            Surfactant            5 to 12  pts.                                            Others                5 to 30  pts.                                            ______________________________________                                    

As others, for example, mentioned are anti-freezing agent, tackifier, etc.

    ______________________________________                                         Granular Wettable Powder (dry flowable powder):                                Compound of this invention                                                                             20 to 90 pts.                                          Solid Carrier           10 to 60 pts.                                          Surfactant              1 to 20  pts.                                          Granules:                                                                      Compound of this invention                                                                             0.1 to 10                                                                               pts.                                          Solid carrier           90 to 99.9                                                                              pts.                                          Others                  1 to 5   pts.                                          Formulation Example 1: Wettable Powder                                         Compound No. 1 of this invention                                                                       20       pts.                                          Zeeklite A              76       pts.                                          (kaolin clay, trade name by Zeeklite Co.)                                      Sorpol 5039             2        pts.                                          (mixture of nonionic surfactant and anionic                                    surfactant, trade name by Toho Chemical Co.)                                   Carplex (anti-caking agent)                                                                            2        pts.                                          (white carbon, trade name by Shionogi                                          Pharmaceutical Co.)                                                            ______________________________________                                    

The above-mentioned components were homogeneously blended and powdered to give a wettable powder.

    ______________________________________                                         Formulation Example 2: Wettable Powder                                         ______________________________________                                         Compound No. 1 of this invention                                                                          40    pts.                                          Zeeklite A                 54    pts.                                          (kaolin clay, trade name by Zeeklite Co.)                                      Sorpol 5039                2     pts.                                          (mixture of nonionic surfactant and anionic                                    surfactant, trade name by Toho Chemical Co.)                                   Carplex (anti-caking agent)                                                                               4     pts.                                          (white carbon, trade name by Shionogi                                          Pharmaceutical Co.)                                                            ______________________________________                                    

The above-mentioned components were homogeneously blended and powdered to give a wettable powder.

    ______________________________________                                         Formulation Example 3: Emulsifiable concentrate                                ______________________________________                                         Compound No. 1 of this invention                                                                          5     pts.                                          Xylene                     75    pts.                                          Dimethylformamide          15    pts.                                          Sorpol 2680                5     pts.                                          (mixture of nonionic surfactant and anionic                                    surfactant, trade name by Toho Chemical Co.)                                   ______________________________________                                    

The above-mentioned components were homogeneously blended to give an emulsion.

    ______________________________________                                         Formulation Example 4: Flowable Liquid                                         ______________________________________                                         Compound No. 1 of this invention                                                                         25     pts.                                          Agrisole S-710            10     pts.                                          (nonionic surfactant, trade name by Kaoh Co.)                                  Runox 1000C               0.5    pts.                                          (anionic surfactant, trade name by Toho                                        Chemical Co.)                                                                  Aqueous 1% Rodopol water  20     pts.                                          (tackifier, trade name by Rhone-Poulenc Co.)                                   Water                     44.5   pts.                                          ______________________________________                                    

The above-mentioned components were homogeneously blended to give a flowable liquid.

    ______________________________________                                         Formulation Example 5: Flowable Liquid                                         ______________________________________                                         Compound No. 1 of this invention                                                                         40     pts.                                          Agrisole S-710            10     pts.                                          (nonionic surfactant, trade name by Kaoh Co.)                                  Runox 1000C               0.5    pts.                                          (anionic surfactant, trade name by Toho                                        Chemical Co.)                                                                  Aqueous 1% Rodopol water  20     pts.                                          (tackifier, trade name by Rhone-Poulenc Co.)                                   Water                     29.5   pts.                                          ______________________________________                                    

The above-mentioned components were homogeneously blended to give a flowable liquid.

    ______________________________________                                         Formulation Example 6: Granular Wettable Powder                                (dry flowable powder)                                                          ______________________________________                                         Compound No. 1 of this invention                                                                         75    pts.                                           Isobam No. 1              10    pts.                                           (anionic surfactant, trade name by Kuraray                                     Isoprene Chemical Co.)                                                         Vanilex N                 5     pts.                                           (anionic surfactant, trade name by Sanyo                                       Kokusaku Pulp Co.)                                                             Carplex #80               10    pts.                                           (white carbon, trade name by Shionogi                                          Pharmaceutical Co.)                                                            ______________________________________                                    

The above-mentioned components were homogeneously blended and finely powdered to give a dry flowable powder.

    ______________________________________                                         Formulation Example 7: Granule                                                 ______________________________________                                         Compound No. 1 of this invention                                                                        1     pts.                                            Bentonite                55    pts.                                            Talc                     44    pts.                                            ______________________________________                                    

The above-mentioned components were blended and powdered, and a small amount of water was added thereto,stirred, further blended and kneaded. Using an granulator, the mixture was granulated and dried to give granules.

    ______________________________________                                         Formulation Example 8: Granule                                                 ______________________________________                                         Compound No. 1 of this invention                                                                       1.0    pts.                                            Compound (A)            0.07   pts.                                            DBSN                    3      pts.                                            Epoxidated Soybean Oil  1      pts.                                            Bentonite               30     pts.                                            Talc                    64.93  pts.                                            ______________________________________                                    

The above-mentioned components were blended and powdered, and a small amount of water was added thereto and kneaded. Using an extrusion granulator, the mixture was granulated and dried to give granules.

Compound (A) is pyrazosulfuron ethyl (common name); and DBSN is sodium dodecylbenzenesulfonate.

Where the above-mentioned wettable powder, emulsion, flowable liquid and granular wettable powder are actually used, they are diluted with water to 1/50 to 1/1000 dilutions, and the dilution may be applied in a dose of from 0.001 to 50 kg/ha, preferably from 0.01 to 10 kg/ha, as the active ingredient.

The herbicides containing the compounds of the present invention may be applied to paddy fields both for soil treatment and for foliage treatment.

As examples of paddy weeds, mentioned are weeds of the family Alismataceae such as Alisma canaliculatum, Sagittaria trifolia, Sagittaria pygmaea, etc.; weeds of the family Cyperaceae such as Cyperus difformis, Cyperus serotinus, Scirpus juncoides, Eleocharis kuroguwai, etc.; weeds of the family Scrothulariaceae such as Lindemia pyxidaria, etc.; weeds of the family Potenderiaceae such as Monochoria vaginalis, etc.; weeds of the family Potamogetonaceae such as Potamogeton distinctus, etc.; weeds of the family Lythraceae such as Rotala indica, etc.; and weeds of the family Gramineae such as Echinochloa crus-galli, etc.

The compounds of the present invention are also usable as herbicides for soil treatment, soil incorporation treatment and foliage treatment. Furthermore, they may also be applied to control various weeds in non-agricultural fields, such as playgrounds, vacant lands, railroad sides, etc., in addition to agricultural and horticultural fields such as paddy fields, upland fields, orchards, etc.

The following test examples concretely demonstrate the usefulness of the compounds of the present invention as herbicides.

Test Example 1:

Test of compounds of the invention as to their herbicidal effect, by soil treatment under paddy field condition:

An Alluvium soil was put in 1/5000 are-Wagner pots, and water was added thereto to knead the soil therein. Accordingly, a paddy field condition was prepared, having a depth of water of 4 cm. Seeds of Echinochloa crus-galli, Monochoria vaginalis, Rotala indica and Scirpus juncoides were sown mixedly in the pots, and 2.5 leaves-stage rice plants were transplanted therein. The pots were put in a greenhouse at 25° to 30° C. so as to grow the plants. On the first day after the seeding, pre-determined doses of the compounds of the present invention, that had been prepared into herbicidal formulations in accordance with the formulation examples mentioned above, were applied on the water surfaces in the pots. Three weeks after the application, the herbicidal effect of the test compounds against the rice plants and the weeds was checked. The effect was evaluated by 5-rank evaluation, in which "0" means that the compound had no influence on the plants while "5" means that the plants were completely withered. The test results are shown in Table 5 below.

Test Example 2:

Test of compounds of the invention as to their herbicidal effect, by foliage treatment under paddy field condition.

An Alluvium soil was put in 1/5000 are-Wagner pots, and water was added thereto to knead the soil therein. Accordingly, a paddy field condition was prepared, having a depth of water of 4 cm. Seeds of Echinochloa crus-galli, Monochoria vaginalis, Rotala indica and Scirpus juncoides were sown mixedly in the pots, and 2.5 leaves-stage rice plants were transplanted therein. The pots were put in a greenhouse at 25° to 30° C. so as to grow the plants. After the weeds of Echinochloa crus-galli, Monochoria vaginalis, Rotala indica and Scirpus juncoides had grown to one leaf- to two leaves-stage and the rice plants to four leaves-stage, pre-determined amount of the compounds of the present invention, that had been prepared into herbicidal formulations in accordance with the formulation examples mentioned above, were applied over the plants in the pots. Three weeks after the application, the herbicidal effect of the test compounds against the rice plants and the weeds was checked. The effect was evaluated in the same manner as in Test Example 1. The test results are shown in Table 6 below.

In the following tables, A means Echinochloa crus-galli; B means Scirpus juncoides, C means Monochoria vaginalis, D means Rotala indica, and a means rice plants.

                  TABLE 5                                                          ______________________________________                                                   Amount of Compound                                                   Compound No.                                                                             g/a            A     B    C   D    a                                 ______________________________________                                         1         10             5     5    5   5    0                                 2         10             5     5    5   4    0                                 3         10             5     5    5   5    0                                 4         10             5     5    5   5    0                                 5         10             5     5    5   5    0                                 7         10             5     5    5   4    0                                 8         10             5     5    4   2    0                                 9         10             5     5    5   4    0                                 10        10             5     4    5   2    0                                 11        10             5     4    5   5    0                                 12        10             5     2    5   4    0                                 13        10             5     4    5   4    0                                 14        10             5     4    5   4    0                                 16        10             5     5    5   4    0                                 18        10             5     4    4   4    0                                 19        10             5     4    4   4    0                                 22        10             5     5    5   5    0                                 25        10             5     5    5   5    0                                 26        10             5     5    5   5    0                                 27        10             5     5    5   5    0                                 33        10             5     5    5   5    0                                 34        10             5     5    5   5    0                                 37        10             5     5    4   4    0                                 38        10             5     5    4   4    0                                 39        10             5     5    5   5    0                                 40        10             5     5    4   4    0                                 44        10             5     5    4   5    0                                 45        10             5     5    5   4    0                                 50        10             5     5    4   4    0                                 55        10             5     5    4   4    0                                 57        10             5     5    4   5    0                                 58        10             5     5    5   5    0                                 59        10             5     5    5   5    0                                 60        10             5     5    5   5    0                                 61        10             5     5    4   4    0                                 62        10             5     5    5   4    0                                 63        10             5     5    5   4    0                                 64        10             5     5    5   4    0                                 65        10             5     5    5   4    0                                 66        10             5     5    5   4    0                                 67        10             5     5    5   5    0                                 87        10             5     5    5   5    0                                 88        10             5     5    5   5    0                                 92        10             5     5    5   5    0                                 95        10             5     5    4   4    0                                 97        10             5     5    5   5    0                                 98        10             5     5    5   4    0                                 99        10             5     5    5   5    0                                 100       10             5     5    5   5    0                                 101       10             5     5    5   5    0                                 104       10             5     5    5   4    0                                 105       10             5     5    5   4    0                                 106       10             5     5    5   4    0                                 107       10             5     5    5   4    0                                 108       10             5     5    5   5    0                                 116       10             5     5    5   4    0                                 124       10             5     5    5   5    0                                 125       10             5     5    5   5    0                                 127       10             5     5    5   5    0                                 128       10             5     5    4   4    0                                 133       10             5     5    5   5    0                                 136       10             5     5    5   5    0                                 138       10             5     5    5   4    0                                 146       10             5     5    5   5    0                                 149       10             5     5    5   5    0                                 170       10             5     5    5   4    0                                 171       10             5     5    5   4    0                                 173       10             5     5    5   5    0                                 174       10             5     5    5   4    0                                 ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                                   Amount of Compound                                                   Compound No.                                                                             g/a            A     B    C   D    a                                 ______________________________________                                         4         10             5     4    4   3    0                                 34        10             5     4    4   4    0                                 38        10             5     4    3   4    0                                 59        10             5     4    4   2    0                                 63        10             5     4    4   4    0                                 65        10             5     5    4   4    0                                 66        10             5     5    4   4    0                                 88        10             5     5    4   4    0                                 92        10             5     4    4   4    0                                 98        10             5     4    5   5    0                                 99        10             5     4    5   4    0                                 100       10             5     4    5   4    0                                 101       10             5     5    5   4    0                                 105       10             5     4    4   4    0                                 107       10             5     4    4   4    0                                 108       10             5     4    4   4    0                                 125       10             5     4    5   4    0                                 128       10             5     4    4   4    0                                 134       10             5     4    4   4    0                                 136       10             5     5    5   4    0                                 138       10             5     4    4   4    0                                 146       10             5     5    5   5    0                                 149       10             5     5    5   5    0                                 173       10             5     5    5   5    0                                 174       10             5     4    5   3    0                                 ______________________________________                                     

We claim:
 1. A pyrazole-glycolic acid amide of formula (1): ##STR155## wherein R¹ represents a C₁₋₄ haloalkyl group, a cyano group, or a halogen atom;R² represents an unsubstituted phenyl group or an unsubstituted pyridyl group; R³ represents a halogen atom; R⁴ and R⁵ form, along with the nitrogen atom to which they bond, a 5-membered to 8-membered ring, wherein the ring may contain one or more nitrogen atoms and the ring may be substituted by a C₁₋₄ alkyl group.
 2. A herbicidal composition comprising one or more pyrazole-glycolic acid amide(s) as claimed in claim 1 as the active ingredient(s).
 3. A method for controlling or inhibiting the growth of weeds by applying thereto a herbicidally effective amount of one or more pyrazole-glycolic acid amide(s) as claimed in claim
 1. 